TITLE ARTHROPODICIDAL ANILIDES The substituted anilides of this invention are unknown in the art, with WO 90/07495 being perhaps the most relevant publication in this regard. The anilides of this invention include all geometric and stereo- isomers, arthropodicidally suitable salts thereof, arthropodicidal compositions containing them and their use to control arthropods in agronomic and nonagronomic environments. The term "compounds" includes all such isomers and salts thereof. The compounds are:

wherein

Q is selected from the group

Q-3

R¹ is selected from the group Cl, Br, CF₃, OCF₃, OCF₂H and OS0₂CF₃; R¹ being OCF₃ when Q is Q-3 and Y is CH₃, CH₂CH₂CH₂CH₃ or CH₂Ph; R² is selected from the group H, F, Cl, Br, CF₃, OCF₃,

OCF₂H and OCH₂CF₃; Y is selected from the group Ci-Cg alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₃ alkylsulfonyl, C₃-C₆ cycloalkyl, C₃-C₆ cycloalkylalkyl, NR⁶R⁷, N*=CR⁸R⁹, OR⁶, COR⁴, CO2R⁴ and Ci-Cg alkyl substituted by a group selected from halogen, Cχ-C3 alkoxy, CN, N0₂, S(0)_nR⁴, COR⁸, C0₂R⁸ and phenyl, the phenyl optionally substituted by a group selected from halogen, CN, C3.-C2 alkyl, ^cl~^c2 alkoxy, ^-C₂ haloalkyl and 0ι~C₂ haloalkoxy; Y being NR⁶R⁷, N«CR⁸R⁹ or OR⁶ when Q is Q-2; and Y being other than COR⁴ and C0₂R⁴ when Q is Q-3;

R3 i_s selected from the group C0₂Me, C0₂Et, Ph, 4-F-Ph, 4-Cl-Ph and C^Cs alkyl;

R⁴ is 0^0₃ alkyl; R⁴ being C₂-C₃ alkyl when Y is COR⁴ or C0₂R⁴, Q is Q-1 and Z¹ is O;

R5 is selected from the group H and ^-0₃ alkyl;

R6 is selected from the group H, C_!-C alkyl, ^-0₄ haloalkyl, C₂-C₄ alkenyl, C -C₄ alkynyl, S0₂NR⁸R⁹ S0₂R¹⁰, COR⁸, CONR⁸R⁹, C0₂R⁸, phenyl optionally substituted with halogen or Ci-0 alkoxy, and benzyl optionally substituted with halogen; R⁷ is selected from the group H, C_J.-C₄ alkyl and COR⁸; R⁸ is selected from the group H, C_J-C alkyl, ^-0₄ haloalkyl and phenyl optionally substituted by a group selected from halogen, CN, N0₂, CF₃ and

OCF₃; R⁹ is selected from the group H and 0^0₄ alkyl; R⁸ and R⁹ can be taken together as -CH₂CH₂CH₂-, -CH₂CH₂CH₂CH₂- and -CH₂-H₂CH₂CH₂CH₂-;

R¹⁰ is selected from the group ^-0₄ alkyl and ^-0₄ haloalkyl; R¹¹ is selected from the group H and C₂.-C₄ alkyl; R¹¹ being H when Q is Q-1 and Y is CH₃ or C(0)CH₃; Z is selected from the group CH , 0, S and NR⁶; and Z¹ is selected from the group 0 and NR¹¹.

Preferred for reasons including greater arthropodicidal efficacy are:

A) Compounds of Formula I wherein Q is Q-1;

B) Compounds of Formula I wherein Q is Q-2;

C) Compounds of Formula I wherein Q is Q-3;

D) Compounds of Preferred A wherein Y is NR⁶R⁷, N=CR⁸R⁹ or OR⁶;

E) Compounds of Preferred D wherein R⁶ is H or C₁-C₃ alkyl;

F) Compounds of Preferred A wherein Y is CH₃ or CH2CH3; and G) Compounds of Preferred A wherein R³ is C0₂Me.

Specifically preferred is Compound E:

H) methyl 2-[[-1-[4 (trifluoromethyl)phenyl]- hydrazino]carbonyl]-2,3-dihydro-7-(trifluoro- methyl) [l]benzopyrano [4,3-C]pyrazole-3a(4H)- carboxylate.

Specifically preferred are Compounds G:

I) methyl 2,3-dihydro-2-[[N-methyl-N-[4-

(trifluoromethyl)phenyl]amino]carbonyl]-7- (trifluoromethyl) [1]benzopyrano[4,3-c]pyrazole- 3a(4H)-carboxylate,

J) methyl 7-chloro-2,3-dihydro-2-[[N-methyl-N-[4- (trifluoromethyl)phenyl]amino]carbonyl] [1]benzo¬ pyrano [4,3-c]pyrazole-3a(4H)-carboxylate,

K) methyl 2-[[N-(4-chlorophenyl)-N-methylamino]- carbonyl]-2,3-dihydro-7-(trifluoromethyl)- [1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate,

L) methyl 2-[[N-(4-bromophenyl)-N-methylamino]- carbonyl]2,3-dihydro-7-(trifluoromethyl)-

[1]benzopyrano[4,3-c]pyrazole-3a(4H)-carboxylate, and

) methyl 2,3-dihydro-2-[[N-methyl-N[4-(trifluoro- methoxy)-phenyl]amino]carbonyl] -1-(trifluoro¬ methyl) [1]benzopyrano[4,3-c]pyrazole-3a(4H)- carboxylate.

In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl" includes straight chain or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, butyl, pentyl or the different hexyl isomers. Alkenyl includes straight chain or branched alkenes, such as 1-propenyl, 2-propenyl, 3-propenyl and the different hexenyl isomers. Alkynyl includes straight chain or branched chain aικynyι groups such as 1-pentynyl, 2-pentynyl, 3-pentynyl and the different hexynyl isomers. Alkoxy includes methoxy, ethoxy, n-propyloxy and isopropyloxy. The term "halogen", either alone or in compound words such as

"haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl can be partially or fully substituted with halogen atoms, which can be the same or different. Examples of haloalkyl include CH₂CH₂F, CF CF₃ and CH₂CHFC1. The total number of carbon atoms in a substituent group is indicated by the Ci~Cj prefix where i and j are numbers from 1 to 6. For example, C₁-C₃ alkoxy would designate methoxy through propoxy. The term "cycloalkyl" alone or in compound words such as

"cyclohaloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups. Cycloalkylalkyl includes cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl groups. DETAILS OF THE INVENTION

The preparation of Formula I (Q-1) compounds where Y is other than NR⁶R⁷, N=CR⁸R⁹ or OR⁶ can be accomplished by the N-alkylation of Formula II (Q-1) derivatives. For example. Formula II (Q-1) derivatives are treated with a base such as sodium hydride, potassium hydride, potassium tert-butoxide, lithium diisopropyl amide and the like in an inert solvent such as ether, tetrahydrof ran, dioxane, dimethylformamide and dimethylsulfoxide. Subsequent treatment with an electrophilic reagent such as alkyl halides, dialkylsulfates, alkenyl halides, alkynyl halides, substituted alkyl halides, optionally substituted benzyl halides, alkylsulfonyl halides and the like will result in the formation of Formula I compounds as illustrated in Scheme 1. SCHEME 1

¹¹ - {_--)

Formula I compounds where Y is NR⁶R⁷ can be prepared by the N-amination of Formula II derivatives. For example. Formula II derivatives are treated with a base such as sodium hydride, potassium hydride, potassium tert-butoxide, lithiumdiisopropyl amide and the like in an inert solvent such as ether, tetrahydrofuran dioxane, dimethylformamide and di ethylsulfoxide. Subsequent treatment of the anion with an electrophilic aminating reagent such as O-diphenylphosphinylhydroxylamine, hydroxylamine-O-sulfonic acid (HOSA) , 0-(2,4-dinitro- phenyl) ydroxylamine, O-mesitylenesulfonylhydroxylamine (MSH) , and the like will result in the formation of Formula I compounds where Y is NR⁶R⁷ as illustrated in Scheme 2. Methods for the preparation and use of such electrophilic aminating reagents can be found in Synthesis 1977, 1. For instance, amides, imides, pyrroles and other related compounds can be aminated by aminating reagents in good yields.

II

Alternatively, Formula I compounds can be prepared by coupling of the intermediate compounds of the Formula III with a compound of Formula Ilia in the presence of phosgene or a phosgene equivalent. Typical reaction conditions involve combination of a phosgene equivalent with the Formula III compound in a solvent such as tetrahydrofuran or chloroform followed by the addition of the Formula Ilia compound. This chemistry is depicted in Scheme 3.

SCHEME 3

Compounds of Formula I where Y is NH₂, NHR⁷ or OH can be further derivatized by standard alkylation, acylation, sulfonylation and related reactions by procedures well documented in the art. Furthermore, compounds of Formula I where Y is NH₂ can be condensed with aldehydes and ketones to form the corresponding hydrazone derivatives of Formula I. These procedures are also well documented in the art. The preparation of Formula II (Q-1) derivatives is described in WO 90/10623, WO 88/0799 and WO 91/08207. For instance, tricyclic pyrazolines of Formula III (Q-1) can be condensed with equimolar amounts of isocyanates of Formula V to give Formula II (Q-1) compounds. Compounds of Formula II (Q-2) where Z is O, S, NR⁶ can be prepared by the reaction of Formula IV compounds with isocyanates of Formula V. Typical reactions involve the combination of equimolar amounts of IV and V in a conventional organic solvent such as, but not limited to, ethyl acetate, methylene chloride, chloroform, benzene or toluene. A base such as an alkali metal, tertiary a ine, alkali metal alkoxide or metal hydride can be used. Scheme 4 illustrates this transfora tion.

SCHEME 4

s 0, S, NR⁶

IV where Z is O, S, NR

Alternatively, compounds of Formula II (Q-2) , where Z is O or S, can be prepared by the reaction of semicarbazones of Formula VI with paraformaldehyde or other equivalents known to those skilled in the art. Typical reactions involve the combination of an excess in molar amounts of paraformaldehyde (1.1 equivalents to 40 equivalents) with 1 equivalent of a Formula VI compound optionally in the presence of less than one molar equivalent of an acid catalyst (0 equivalents to 0.9 equivalents) . Typical acid catalysts include alkyl or aryl sulfonic acids (such as methyl, camphor or p-toluene sulfonic) and mineral acids (such as hydrochloric or sulfuric) . Conventional polar organic solvents such as acetonitrile, dimethylformamide, tetrahydrofuran, methanol or ethanol can be used. The reaction temperature can vary from 0°C to the reflux temperature of the particular solvent being used and the rec.-.tion is usually complete in less than 24 hours. Scheme 5 illustrates this transformation. SCHEME 5

VI Z is 0 or S

Alternatively, compounds of Formula II (Q-2), where Z is 0, S or NR⁶, can be prepared by the reaction of compounds of Formula VI with compounds of Formula VII (see Scheme 6) . Typical reactions involve combination of an excess in molar amounts of a Formula VII compound (1.1 equivalents to 5.0 equivlents) with one equivalent of a Formula VI compound in the presence of a base such as a tertiary a ine (such as triethylamine, pyridine or DBϋ),an alkali metal, an alkali metal hydride or an alkali metal alkoxide or hydroxide (such as sodium methoxide, potassium-t-butoxide, sodium hydroxide or potassium hydroxide) . Conventional polar organic solvents such as methanol, ethanol, propanol, dimethylformamide, THF, dichloromethane or acetonitrile can be used. The reaction temperatures can vary from 0°C to the reflux temperature of the particular solvent being used and the reaction is usually complete in less than 24 hours.

Alternatively, when Z is NR⁶ and L¹ and L² are taken together as

SCHEME 6

VI + H_jC ¹.-² *" II (Q-2) base II

wherein:

L¹, L² are Cl, Br, I, imidazole, or L¹ and L² may be taken together to equal «=0, -S or -V {CE₃) jPl$

(where Z is NR⁶) . Compounds of Formula IV can be prepared by the reaction of Formula VIII compounds with either compounds of Formula VII or a formaldehyde equivalent using methods analogous to those shown for the preparation of Formula II (Q-2) compounds in Schemes 5 and 6. The preparation of Formula IV compounds is shown in Scheme 7.

SCHEME 7

VIII Z is 0 or S

Compounds of Formula VI can be prepared by the reaction of Formula VIII compounds with isocyanates of Formula V as shown in Scheme 8. Typical reactions involve the combination of equimolar amounts of VIII and V in the presence of 1 molar equivalent of water in a polar organic solvent such as tetrahydrofuran or dimethylformamide. The reaction is usually complete in less than 24 hours.

SCHEME 8

Alternatively, Formula VI compounds can be prepared by the reaction of compounds of Formula IX with semicarbazides of Formula X. Conditions for this reaction optionally include an acid catalyst such as hydrochloric, sulfuric or p-toluene sulfonic acid. Reaction temperatures can range from 0 to 150°C with the reflux temperature of the solvent used generally preferred. Suitable solvents include, but are not limited to, methanol, ethanol, isopropanol, tetrahydrofuran and dioxane. Scheme 9 illustrates this transformation.

SCHEME 9

The preparation of Formula VIII compounds can be accomplished by the reaction of Formula IX compounds with an excess of equivalents (1.1 to 10.0 equivalents) of hydrazine, hydrazine monohydrate, hydrazine acetate, hydrazine hydrochloride and the like. The reaction is conducted in an alcohol solvent such as methanol, ethanol, n-propanol, isopropanol, n-butanol and the like or acetic acid and the temperature is governed by the reflux temperature of the particular solvent. The reaction is generally complete in 24 hours. Scheme 10 illustrates this transformation.

SCHEME 10

NH₂NH₂,

IX »^• VIII

NH₂NH₂»H₂0 or NH₂NH₂*HOAc

Compounds of Formula IX where Z is O can be prepared by the α-hydroxylation of ketones of Formula XI using procedures that are well-known to one skilled in the art . See, for instance, J. Am. Chem. Soc , 1974, ££, 5944; Tetrahedron Lett . , 1988, 2__, 2835; J. Org. Chem. , 1986, L, 2402. Scheme 11 illustrates this transformation .

SCHEME 11

Numerous alternative procedures exist for the preparation of α-hydroxyketones of Formula IX (where Z is 0) including the procedure whereby the silyl enol-ether derived from XI is treated with meta-chloroperoxybenzoic acid followed by de-silylation with fluoride (Org. Synth., SA, 118) . α-Keto sulfides of Formula IX where Z is S can be prepared from ketones of Formula XI using procedures known to the art such as treatment of XI with tetramethylthiuram disulfide followed by alkaline hydrolysis fJ. Amar. Chem. Sor... 1985, 2 __1, 4175) . α-Amino ketones of Formula IX where Z is NR⁶ can be prepared from ketones of Formula XI using procedures known in the art such as treatment of ketones XI with cyclohexanespiro-3'-oxaziridine in the presence of base if necessary .Synthesis. l££i, 327) .

Compounds where Z is NHR^i©, can be prepared by the reaction of Formula XI compounds with compounds of the type XII using a procedure similar to those described in the art (Synthesis, 1991, 327) . The conditions for this reaction are the combination of equimolar amounts of Formulae XI and XII derivatives in the presence of a base as a catalyst, such as, but not limited to, DABCO, DBU, sodium hydroxide and the like. Suitable solvents include, but are not limited to, toluene, dioxane and water. Scheme 12 illustrates this transformation.

SCHEME 12

XI XII IX θ

Z is NHR°C1

The starting ketones of Formula XI are known in the art or can be obtained by methods analogous to known procedures. Those skilled in the art will recognize the Formula XI compounds to be indanones.

One skilled in the art will recognize that the transformation of Formula XI compounds into Formula IX compounds may require the use of protecting groups to prevent undesired side reactions of functionalities that may be sensitive to the reaction conditions (for example, an indoxyl nitrogen atom may require a protecting group to render it unreactive in an α-hydroxylation of the carbonyl group) . Since numerous alternative synthetic methods for the preparations of Formula IX compounds exist, a further discussion of protecting-group chemistry will be omitted.

Semicarbazides of Formula X can be prepared using procedures well-known to those skilled in the art.

Compounds of Formula II (Q-2) where Z is CH₂ can be prepared by the reaction of Formula IV compounds with isocyanates of Formula V employing equimolar amounts of IV and V in a conventional organic solvent such as, but not limited to, ethyl acetate, methylene chloride, chloroform, benzene or toluene. A base such as an alkali metal, tertiary amine or metal hydride can be used. Scheme 13 illustrates this transformation.

SCHEME 13

IV Z is CH_'

The preparation of Formula IV compounds where Z is CH₂ can be accomplished by the reaction of Formula XIII compounds with a reducing agent such as LiAlH₄ or BH₃ (see J. Org. Chem., 19733j_, 921). The typical reaction involves the combination of an excess in molar amounts of the reducing agent (1.1 equivalents to 5.0 equivalents) with 1 equivalent of a Formula XIII compound.

Conventional aprotic organic solvents such as diethyl ether, tetrahydrofuran or 1,2-dimethoxyethane can be used. The reaction temperature can vary from 0°C to the reflux temperature of the particular solvent being used and the reaction is usually complete in less than 24 hours. Scheme 14 illustrates this transformation.

SCHEME 14

XIII

.

The preparation of Formula XIII compounds can be accomplished by the reaction of Formula XIV compounds with an excess of equivalents (1.1 to 10.0 equivalents) of hydrazine, hydrazine monohydrate, hydrazine acetate, hydrazine hydrochloride and the like. The reaction is conducted in an alcohol solvent such as methanol, ethanol, a-propanol, isopropanol, n-butanol and the like or acetic acid and the temperature is governed by the reflux temperature of the particular solvent. The reaction is generally complete in 24 hours. Scheme 15 illustrates this transformation. Alternatively, Formula XIII compounds can be prepared from Formula XlVa derivatives as described for the preparation of Formula VII compounds (Scheme 15) .

SCHEME 15

J is Cl, I, Br and OS0₂CH₃

Compounds of Formula XIV where R³ is equal to H can be prepared by the reduction of Formula XV compounds. This transformation can be effected by catalytic hydrogenation (House, Modern Synthetic Reactions, 1972, pp. 1-44) or more conveniently through the use of an excess of equivalents (1.5 to 4.0 equivalents) of zinc in refluxing acetic acid as solvent (J. Med. Chem., 1986 29. 2181). The reaction is usually complete in 24 hours. Scheme 16 illustrates this transformation.

SCHEME 16

Compounds of Formula XV can be prepared by the reaction of Formula XI derivatives with Formula XVI compounds. One skilled in the art will recognize this reaction as an Aldol condensation (House, Modern Synthetic Reactions, 1972, pp.629-733) which is a well-known transformation; see Scheme 17.

SCHEME 17

Alternatively, compounds of Formula XIV can be prepared by hydrolysis of Formula XVII compounds. One skilled in the art will recognize this transformation as conventional and well-understood. Scheme 18 illustrates this common reaction. SCHEME 18

Formula XVII compounds can be prepared by the alkylation of Formula XI derivatives with Formula XVIII compounds. The reaction can be accomplished by the reaction of equimolar amounts of Formula XI and XVIII compounds in the presence of a base such as an alkali metal, tertiary amine, metal hydride and the like in a conventional organic solvent such as, but not limited to, ether, tetrahydrofuran, 1,2-dimethoxyethane, dimethylformamide, dimethylsulfoxide, methanol, ethanol and propanol. The reaction is usually conducted at temperatures between 0^CC and the reflux temperature of the solvent utilized. The reaction is usually complete in 48 hours. Scheme 19 (reaction A) illustrates this transformation.

Additionally, the ketone XI serves as a useful intermediate for compounds of Formula XlVa. Formula XlVa compounds can be prepared by the alkylation of Formula XI derivatives with Formula XVIIIa compounds. The reaction can be accomplished by the reaction of one equivalent of Formula XI compounds and one to ten equivalents of Formula XVIIIa compounds in the presence of a base such as an alkali metal, tertiary amine, metal hydride and the like in a conventional organic solvent such as, but not limited to, ether, tetrahydrofuran, 1,2-dimethoxyethane, dimethylformamide, dimethylsulfoxide, methanol, ethanol and propanol. The reaction is usually conducted at temperatures between 0°C and the reflux temperature of the solvent utilized. The reaction is usually complete in 48 hours. Scheme 19 (reaction B) illustrates this transformation.

The starting ketones of Formula XI are known in the art or can be obtained by methods analogous to known procedures.

The preparation of Formula II (Q-3) derivatives is described in WO 90/07495.

The following Examples serve to further illustrate the invention. EXAMPLE 1

Methyl 2.3-dihydro-2-..N-methyl-N-.4-(trifluoromethyl)- phenyl1amino.carbonyl1-7-(trifluoromethyl ) .11- benzopyrano.4,3-c.pyra__ole-3a(4H.-__arbo_:ylate To a mixture of 60% sodium hydride (0.19 g,

4.75 mmol) in 10 mL of dimethylformamide was added methyl 2,3-dihydro-7-(trifluoromethyl)-2-[[[4-(trifluoromethyl)- phenyl]amino]carbonyl]-[1]benzopyrano[4,3-c]pyrazole- 3a(4H)-carboxylate (1.0 g, 2.05 mmol) in one portion. The color of the reaction turned yellow and the evolution of hydrogen gas was noted. After 10 minutes, methyl iodide (0.3 mL, 4.78 mmol) was added in one portion via syringe and the mixture was then heated at 50°C for one hour. After this time, TLC showed near completion of the reaction, with only a faint trace of residual starting compound. After cooling to room temperature overnight, the mixture was partitioned between 5% aqueous sodium bicarbonate and ether, the aqueous extracts were washed with ether and the combined ether extracts were dried over magnesium sulfate and concentrated to 1.47 g of a pale green, oily solid. Chromatography on silica gel (1:1 ethyl acetate:hexane) afforded 1.12 g of a clear colorless oil which set up to a white solid. Trituration with cold methanol afforded 0.28 g of a white solid, m.p. 105-111°C. The filtrate was concentrated and triturated with cold hexane to afford a second crop of 0.38 g of white solid, m.p. 107-110°C. *H NMR of both crops were identical.

^ NMR (CDC1₃) δ 3.47 (s, 3H) , 3.76 (s,3H), 3.90 (d, IH), 4.09 (d, IH), 4.15 (d, IH) , 5.00 (d, IH) , 7.13 (s, 3H), 7.32 (d, 2H), 7.62 (d, 2H) . EXAMPLE 2 Methyl 2-..-1-.4-(trifluoromethyl.phenyl .hydrazinol r.arbonyl .-2.3-r_i__ydro-7-(tri luoromethyl. TU- bengopyrano.4.3-c.pγrazole-3a (4H. -carboxylate To a mixture of 60% sodium hydride (0.16 g, 4 mmol) in 10 mL of dimethylformamide was added methyl 2,3- dihydro-7-(trifluoromethyl)2-[[[4-(trifluoromethyl)- phenyl]amino]carbonyl]-[1]benzopyrano[4,3-c]pyrazole- 3a(4H)]-carboxylate (1.0 g, 2.05 mmol) at 0°C in one portion. The color of the reaction turned yellow and the evolution of hydrogen gas was noted. The reaction was warmed to ambient temperature over 30 minutes, then O-diphenylphosphinylhydroxylamine (0.75 g, 3.20 mmol) was added in one portion resulting in a white suspension. An extra 10 ml portion of dimethylformamide was added and the reaction was stirred for one hour. After this time the mixture was partitioned between saturated aqueous sodium bicarbonate and ether, the aqueous phase was extracted with ether. The combined ether extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by chromatography on silica gel (40% ethyl acetate/hexane) to afford an oily product. Trituration with ether and hexanes afforded 0.37 g of a white solid, m.p. 118-121°C. R NMR (CDC1₃) δ 7.64-7.50 (m, 5H) , 7.22-7.19 (m, 2H), 5.2 (bs, 2H), 5.05 (d, IH) , 4.35 (d, IH) , 4.18 (d, IH), 3.95 (d, IH), 3.79 (s, 3H) .

EXAMPLE 3 Step A: 5-Fluoro-2-(4- luorophenyl. -2.3-riJhvdro-1H-inri. n- 1-one

To a solution of 50.0 g (0.324 mol) 4-fluorophenyl- acetic acid in 68 ml of methanol was added 1.2 g (6.5 mmol) of p-toluenesulfonic acid. The solution was heated at reflux overnight and then cooled to room temperature and partitioned between dichloromethane and saturated sodium bicarbonate. The dichloromethane layer was washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to afford 43.7 g of a clear, colorless oil. To a solution of 5.7 g (0.14 mol) of 60% sodium hydride in 120 ml of dimethylformamide under nitrogen was added 30.0 g (0.162 mol) of the crude methyl 4-fluoro- phenylacetate dropwise such that hydrogen evolution was moderate and the temperature of the reaction was maintained at less than 50°C. Once hydrogen evolution had ceased, a solution of 33.2 g (0.162 mol) of 3-fluoro- benzylbromide in 30 ml of dimethylformamide was added very cautiously such that the reaction temperature was maintained at less than 60°C. The reaction was maintained at 50 to 60°C with stirring overnight after which time it was partitioned between 5% aqueous NaHCθ₃ and diethyl ether, the aqueous extracts were washed five times with ether and the combined organic extracts were then washed with water. The ether extracts were dried over magnesium sulfate, filtered and concentrated to afford 31.9 g of a yellow oil.

The crude product was combined with 300 ml of methanol, 40 ml of water and 20 ml of 50% aqueous sodium hydroxide and refluxed overnight. After this time, the reaction was concentrated and the crude residue partitioned between water and ether. The aqueous extracts were acidified with IM hydrochloric acid and extracted three times with ether. The ether extracts were dried over magnesium sulfate, filtered and concentrated to 28.7 g of a yellow oil.

The crude product (27.4 g, 0.104 mol) was combined with 32 ml of thionyl chloride and then heated at reflux for 3 hours. Thionyl chloride was removed by concentration at reduced pressure and then the mixture was concentrated several times from carbon tetrachloride. The residue was combined with 130 ml of dichloroethane, cooled under nitrogen to 0°C, and 15.3 g of aluminum trichloride was then added. After stirring overnight the reaction was poured onto a mixture of ice in IN hydrochloric acid, extracted three times with ether and chromatographed on silica gel (10% ethyl acetate/hexane) to afford 8.6 g of product.

^-H NMR (CDC1₃) δ 7.82 (dd, IH) , 7.25-6.95 (m, 6H) , 3.90 (dd, IH), 3.68 (dd, IH), 3.21 (dd, IH) . Step B: 5-Fluoro-2-(4-fluorophenyl>-2.3-dihydro-2- hydroxy-lH-inden-1-one A solution of 7.0 g (0.029 moles) of the product obtained from Step A and 69 mL of toluene was added with stirring to a mixture of 5.7 g (0.034 moles) of triethylphosphite, 0.33 g (0.0014 moles) of benzyl- triethylammonium chloride, 344 mL of toluene and 167 L of 50% aqueous sodium hydroxide solution. A steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour. The resulting mixture was partitioned between hexane/ether and water and the aqueous layer was extracted three times with ether. The combined organic layers were washed twice with water, three times with saturated aqueous sodium bisulfite solution, dried over magnesium sulfate and concentrated. The resulting crude product was triturated several times with hexanes to afford 2.93 g of a pale yellow solid.

^ NMR (CDCI₃) δ 7.83 (dd, IH), 7.32-7.15 (m, 4H) , 6.99 (apparent t, 2H) , 3.56 (s, 2H) , 3.2 (bs, IH) . Step C: 2-r5-Fluoro-2-(4-fluorophenyl.-2.3-dihyriro-?- hydroxy-lH-inden-1-ylidene1-N-r -bromoph<.ny_ 1- hydrazine-carboxamide A solution of 2.8 g (0.0108 moles) of the product obtained from Step B, 0.78 mL (0.016 moles) of hydrazine monohydrate and 15 mL of methanol was heated at reflux for 3 hours. The resulting solution was partitioned between water and methylene chloride and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and concentrated, to afford 3.0 g of a yellow solid.

A solution of 0.8 g of the above product, 0.58 g (0.0029 moles) of 4-bromophenyl isocyanate, 8 mL of tetrahydrofuran and 1 drop of water was stirred at room temperature for two hours then 50 ml of hexane was added. After 15 minutes, a precipitate formed. The solid was filtered to afford 1.17 g of a pale yellow solid, m.p. 235-237°C.

^-H NMR (d₆-DMSO) δ 9.42 (s, IH) , 9.23 (s, IH) , 8.03 (t, IH), 7.59 (d, 2H), 7.44 (d, 2H),7.4-7.1 (m, 7H) , 3.53 (d, IH) , 3.3 (d, overlapping with DMSO, IH) . Step D: 7-Fluoro-4a-(4-fluorophenyl )-4a.5-dihydro-N-.4- b_romo_.__ei.yl1-indenpr1,2-e1-r1>3, \1o__adiazine-

2 (3H. -carboxamide A mixture of 0.80 g (0.0017 moles) of the product obtained in Step C, 0.25 g (0.0027 moles) of paraformal¬ dehyde, 50 mg of p-toluene sulfonic acid monohydrate and 45 mL of acetonitrile was refluxed for 30 minutes. The resulting mixture was partitioned between chloroform and saturated aqueous sodium bicarbonate and the aqueous layer was extracted three times with chloroform. The combined organic layers were dried over magnesium sulfate and concentrated to give a yellow solid. The solid was triturated with methanol/water, and dried under vacuum to afford 0.57 g of a yellow solid, m.p. 208-209°C.

^XH NMR (CDC1₃) δ 8.41 (bs, IH), 7.75 (dd, IH) , 7.43 (apparent q, 4H) , 7.32-7.22 (m, 2H) , 7.15-6.92 (m, 4H) , 5.75 (d, IH) , 4.52 (d, IH) , 3.48 (ABq, 2H) . Step E: 7-Fluoro-4a-( -fluorophenyl. -4a.5-dihydro- indenon ,2-31-.1 ,3, 1oxadia_ine-2(3H)-carboxylic acid -H-bromcpheny )hydraaide To a mixture of 60% sodium hydride (0.16 g, 4 mmol) in 10 mL of dimethylformamide was added N-(4-bromo- phenyl)-7-fluoro-4a-(4-fluorophenyl)4a,5-dihydroindeno- [1,2-e] [1,3,4]oxadiazole-2(3H)-carboxamide (1.0 g, 2.07 mmol) at 0°C in one portion. The color of the reaction turned yellow and the evolution of hydrogen was noted. The reaction was warmed to ambient temperature over 20 minutes, then 0-diphenylphosphoylhydroxylamine (0.73 g, 3.10 mmol) was added in one portion to give a heterogeneous reaction mixture. After the hour, the mixture was partitioned between saturated sodium bicarbonate and ether and the aqueous phase was extracted with ether. The combined ether extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel (40% ethyl acetate/hexane) to give 0.43 g of a yellow solid, m.p. 175-180°C. ⁱH NMR (CDC1₃) δ 7.5-6.8 (m, 11H) , 5.5 (d, IH) , 4.7 (bs, 2H), 4.65 (d, IH) , 3.4 (ABq, 2H) .

By the procedures described herein or through obvious modifications thereof, the compounds of Tables 1-23 can be prepared.

GENERAL STRUCTURES FOR COMPOUNDS OF TABLES 1-14

I_a____-

1

2

4

5

6

8

9 10 11 12 13 14

GENERAL STRUCTURES FOR TABLES 15-18

GENERAL STRUCTURES FQR TABLES 20-23

B

Cl H

Br H

CF₃ H

OCF₃ H

OS0₂CF₃ H

Cl H

Br H

CF₃ H

OCF₃ H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

CF₃ 6-F

OCF₃ 6-F

OS0₂CF₃ 6-F

Cl 6-F

Br 6-F

CF₃ 6-F

OCF₃ 6-F

OS0₂CF₃ 6-F

¹ B

^Z

Cl H

Br H

CF3 H

OCF3 H

OS0₂CF₃ H

Cl H

Br H

CF₃ H

OCF3 H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF3 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

CF₃ 6-F

OCF3 6-F

OS0₂CF₃ 6-F

Cl 6-F

Br 6-F

CF₃ 6-F

OCF3 6-F

OS0₂CF₃ 6-F

Cl H

Br H

CF₃ H

OCF₃ H

OS0₂CF₃ H

Cl H

Br H

CF₃ H

OCF3 H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

CF₃ 6-F

OCF₃ 6-F

OS0₂CF₃ 6-F

Cl 6-F

Br 6-F

CF₃ 6-F

OCF3 6-F

OS0₂CF₃ 6-F

¹ B

² X B

¹ E

² X

Cl 7-CF3 Me OCF3 7-CF3 (CH₂)₂OMe

Br 7-CF3 Me CF3 7-CF3 CH₂SMe

CF₃ 7-CF3 Me OCF3 7-CF3 CH₂SMe

OCF₃ 7-CF3 Me CF3 7-CF3 CH₂C0₂Me

OS0₂C 3 7-CF3 Me OCF3 7-CF3 CH₂C0₂Me

Cl 7-CF3 Et CF3 7-CF3 CH₂Ph

Br 7-CF3 Et OCF3 7-CF3 CH₂Ph

CF₃ 7-CF3 Et CF₃ 7-CF3 allyl

OCF3 7-CF3 Et OCF3 7-CF3 allyl

OS0₂CF₃ 7-CF3 Et f

CF₃ 7-Cl CH₂CN

OCF₃ 7-Cl CH₂C

CF₃ 7-Cl CH₂OMe

OCF₃ 7-Cl CH₂OMe

CF₃ 7-Cl (CH₂)₂OMe

OCF₃ 7-Cl (CH₂)₂OMe

CF₃ 7-Cl CH₂SMe

OCF₃ 7-Cl CH₂SMe

CF₃ 7-Cl CH₂C0₂Me OCF₃ 7-Cl CH₂C0₂Me CF₃ 7-Cl CH₂Ph OCF₃ 7-Cl CH₂Ph

CF₃ 7-Cl allyl

OCF₃ 7-Cl allyl

CF₃ 7-CF3 CH₂CN

OCF₃ 7-CF3 CH₂CN

CF3 7-CF3 CH₂OMe

OCF3 7-CF3 CH₂0Me

CF₃ 7-CF3 (CH₂)₂OMe E^x B Cl H Br H CF₃ H

OCF₃ H

OS0 CF₃ H

Cl H

Br H

CF₃ H

OCF₃ H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

C 3 6-F

OCF3 6-F

OS0₂CF₃ 6-F

Cl 6-F

Br 6-F

CF3 6-F

OCF3 6-F

OS0₂CF₃ 6-F

¹ E^ Cl H Br H

CF₃ H

OCF₃ H

OS0₂CF₃ H

Cl H

Br H

CF3 H

OCF3 H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF3 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

CF₃ 6-F

OCF3 6-F

0S0₂CF₃ 6-F

Cl 6-F

Br 6-F

CF3 6-F

OCF3 6-F

OS0₂CF₃ 6-F

¹ Cl H Br H

C ₃ H

OCF₃ H

OS0 CF₃ H

Cl H

Br H

CF₃ H

OCF3 H

OS0₂CF₃ H

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-C1

Br 6-C1

CF₃ 6-C1

OCF₃ 6-C1

OS0₂CF₃ 6-C1

Cl 6-F

Br 6-F

CF₃ 6-F

OCF3 6-F

OS0₂CF₃ 6-F

Cl 6-F

Br 6-F

∞3 6-F OCF3 6-F

OS0₂CF3 6-F

¹ E^ B

³ X B^ B

³ X

OCF₃ 7-F C0 Me NH₂ Br 7-F C0₂Me NHMe

OCF3 7-F C0₂Et NH₂ Br 7-F C0₂Et NHMe

OCF3 7-F Me NH₂ Br 7-F Me NHMe

OCF3 7-F n-Pr NH₂ Br 7-F n-Pr NHMe

OCF3 7-F i-Pr NH₂ Br 7-F i-Pr NHMe

OCF₃ 7-F 4-F-Ph NH₂ Br 7-F 4-F-Ph NHMe

OCF₃ 7-Cl C0₂Me NH₂ Br 7-Cl CO^e NHMe

OCF₃ 7-Cl C0₂Et NH₂ Br 7-Cl C0₂Et NHMe

OCF₃ 7-Cl Me NH₂ Br 7-Cl Me NHMe

OCF₃ 7-Cl n-Pr NH₂ Br 7-Cl n-Pr . NHMe

OCF₃ 7-Cl i-Pr NH₂ Br 7-Cl i-Pr NHMe

OCF3 7-Cl 4-F-Ph NH₂ Br 7-Cl 4-F-Ph NHMe

OCF3 7-CF₃ C0₂Me KH₂ Br 7-CF3 C0₂Me NHMe

OCF3 7~CF₃ C0 Et NH Br 7-CF3 C0₂Et NHMe

OCF3 7-CF₃ Me NH₂ Br 7-CF3 Me NHMe

OCF3 7-CF₃ n-Pr NH₂ Br 7-CF3 n-Pr NHMe

OCF3 7-CF₃ i-Pr NH₂ Br 7-CF3 i-Pr NHMe

OCF3 7-CF₃ 4-F-Ph NH₂ Br 7-CF3 4-F-Ph NHMe

CF₃ 6-F C0₂Me NHMe OCF3 6-F C0₂Me NHMe

CF₃ 6-F C0₂Et NHMe OCF₃ 6-F C0₂Et NHMe

CF₃ 6-F Me NHMe OCF3 6-F Me NHMe

CF3 6-F n-Pr NHMe OCF₃ 6-F n-Pr NHMe

CF₃ 6-F i-Pr NHMe OCF₃ 6-F i-Pr NHMe

CF₃ 6-F 4-F-Ph NHMe OCF₃ 6-F 4-F-Ph NHMe C ₃ 7-F C0₂Me NHMe OCF₃ 7-F C0₂Me NHMe CF₃ 7-F C0₂Et NHMe OCF₃ 7-F C0₂Et NHMe

C ₃ 7-F Me NHMe OCF₃ 7-F Me NHMe CF₃ 7-F n-Pr NHMe OCF₃ 7-F n-Pr NHMe

CF₃ 7-F i-Pr NHMe OCF3 7-F i-Pr NHMe

C ₃ 7-F 4-F-Ph NHMe OCF3 7-F 4-F-Ph NHMe

¹ B^ B

³ X B

¹ B B

^J X

Br 7-F C0₂Me NH(CO)NHMe CF₃ 7-F C0₂Me NH(CO)NHMe

Br 7-F C0₂Et NH(CO)NHMe CF₃ 7-F C0₂Et NH(CO)NHMe

Br 7-F Me NH(CO)NHMe CF₃ 7-F Me NH(CO)NHMe

Br 7-F n-Pr NH(CO)NHMe CF₃ 7-F n-Pr NH(CO)NHMe

Br 7-F i-Pr NH(CO)NHMe CF3 7-F i-Pr NH(CO) HMe

Br 7-F 4-F-Ph NH(CO)NHMe CF3 7-F 4-F-Ph NH(CO)NHMe

Br 7-Cl C0₂Me NH(CO)NHMe CF₃ 7-Cl C0₂Me NH(CO)NHMe

Br 7-Cl C0₂Et NH(CO)MHMe CF₃ 7-Cl C0₂Et NH(CO)MHMe

Br 7-Cl Me NH(CO)MHMe CF3 7-Cl Me NH(CO)MHMe

Br 7-Cl n-Pr NH(CO)NHMe CF3 7-Cl n-Pr NH(CO) HMe

Br 7-Cl i-Pr NH(CO)NHMe CF₃ 7-Cl i-Pr NH(CO) HMe

Br 7-Cl 4-F-Ph NH(CO)NHMe CF3 7-Cl 4-F-Ph NH(CO)NHMe

Br 7-CF₃ C0₂Me NH(CO)NHMe CF₃ 7-CF3 C0₂Me NH(CO) HMe

Br 7-CF₃ C0₂Et NH(CO) HMe CF₃ 7-CF3 C0 Et NH(CO)NHMe

Br 7-CF₃ Me NH(CO)NHMe CF₃ 7-CF3 Me NH(CO) HMe

Br 7-CF3 n-Pr NH(CO)NHMe CF₃ 7-CF3 n-Pr NH(CO)NHMe

Br 7-CF₃ i-Pr NH(CO)NHMe CF3 7-CF3 i-Pr NH(CO)NHMe

Br 7-CF₃ 4-F-Ph NH(CO)NHMe CF₃ 7-CF3 4-F-Ph NH(CO)NHMe

0CF₃6-F C0₂Me NH(CO)NHMe Br 6-F C0₂Me N-CH₂ OCF36-F C0₂Et NH(CO)NHMe Br 6-F C0₂Et N-CH₂ OCF36-F Me NH(CO)NHMe Br 6-F Me N-CH₂ OCF36-F n-Pr NH(CO)NHMe Br 6-F n-Pr N-CH₂ OCF36-F i-Pr NH(CO)NHMe Br 6-F i-Pr N«CH₂ OCF₃6-F 4-F-Ph NH(CO)NHMe Br 6-F 4-F-Ph N-CH₂ OCF₃7-F C0₂Me NH(CO)NHMe Br 7-F C0₂Me N-CH₂ OCF₃7-F C0₂Et NH(CO)NHMe Br 7-F C0₂Et N-CH₂ OCF₃7-F Me NH(CO)NHMe Br 7-F Me N-CH₂ OCF₃7-F n-Pr NH(CO)NHMe Br 7-F n-Pr N-CH₂ OCF₃7-F i-Pr NH(CO)NHMe Br 7-F i-Pr N-CH₂ OCF₃7-F 4-F-Ph NH(CO)NHMe Br 7-F 4-F-Ph N-CH

³ X B

¹ B^ B

³ X

CF₃ 7-CF3 C0₂Me N-CH₂ OCF₃ 7-CF3 C0₂Me N-CH₂

CF₃ 7-CF3 C0₂Et N-CH₂ OCF3 7-CF3 C0 Et N-CH₂

CF₃ 7-CF3 Me N-CH₂ OCF3 7-CF3 Me N-CH₂

CF₃ 7-CF3 n-Pr N-CH₂ OCF3 7-CF3 n-Pr N-CH₂

CF₃ 7-CF3 i-Pr N-CH₂ OCF3 7-CF₃ i-Pr N-CH₂

CF₃ 7-CF3 4-F-Ph N-CH₂ OCF3 7-CF3 4-F-Ph N-CH₂

Br 6-F C0 Me N-Ofe CF3 6-F C0₂Me N-CMe₂

Br 6-F C0₂Et N-CMe₂ CF₃ 6-F C0₂Et N-CMe₂

Br 6-F Me N-CMe₂ CF₃ 6-F Me N-CMe₂

Br 6-F n-Pr N-CMe₂ CF₃ 6-F n-Pr N-CMe₂

Br 6-F i-Pr N-CMe₂ CF₃ 6-F i-Pr N-CMe₂

Br 6-F 4-F-Ph N-CMe₂ CF3 6-F 4-F-Ph N-CMe₂

Br 7-F C0₂Me N-CMe₂ CF3 7-F C0₂Me N-CMe₂

Br 7-F C0₂Et N-CMe₂ CF3 7-F C0₂Et N-CMe₂

Br 7-F Me N^«CMe₂ CF3 7-F Me N-CMe₂

Br 7-F n-Pr N-CMe₂ CF3 7-F n-Pr N«CMe₂ Br 7-F i-Pr N-CMe₂ CF3 7-F i-Pr N-CMe₂ Br 7-F 4-F-Ph N«CMe₂ CF₃ 7-F 4-F-Ph N-CMe₂ Br 7-Cl C0₂Me N-CMe CF3 7-Cl C0₂Me N-CMe Br 7-Cl C0₂Et N-CMe₂ CF₃ 7-Cl C0₂Et N-CMe₂ Br 7-Cl Me N-CMe CF3 7-Cl Me N-CMe₂ Br 7-Cl n-Pr N-CMe C ₃ 7-Cl n-Pr N-CMe₂ Br 7-Cl i-Pr N_ te₂ CF₃ 7-Cl i-Pr N-CMe₂ Br 7-Cl 4-F-Ph N-CMe₂ CF3 7-Cl 4-F-Ph N-CMe₂ Br 7-CF3 C0₂Me N-CMe₂ CF3 7-CF3 C0₂Me N-CMe₂ Br 7-CF₃ C0₂Et N-CMe₂ CF3 7-CF3 C0₂Et N-CMe₂ Br 7-CF₃ Me N-CMe₂ CF₃ 7-CF3 Me N-CMe₂ Br 7-CF₃ n-Pr N-CMe₂ CF3 7-CF₃ n-Pr N-CMe₂ Br 7-CF₃ i-Pr N-CMe₂ CF3 7-CF₃ i-Pr N-CMe₂ Br 7-CF₃ 4-F-Ph N-0_e₂ CF3 7~CF₃ 4-F-Ph N-CMe₂ B³ X B¹ B^ B³ X

C0₂Me Br 6-F C0₂Me N-CHPh

C0 Et N-CMe₂ Br 6-F C0₂Et N-CHPh

Me N-CMe₂ Br 6-F Me N-CHPh n-Pr N-CMe₂ Br 6-F n-Pr N-CHPh i-Pr N-CMe₂ Br 6-F i-Pr N-CHPh

4-F-Ph N-CMe₂ Br 6-F 4-F-Ph N-CHPh

C0₂Me N-CMe Br 7-F C0₂Me N-CHPh

C0₂Et N-CMe₂ Br 7-F C0₂Et N-CHPh

Me N-CMe₂ Br 7-F Me N-CHPh n-Pr N-CMe₂ Br 7-F n-Pr N-CHPh i-Pr N-CMe₂ Br 7-F i-Pr N-CHPh

4-F-Ph N-CMe₂ Br 7-F 4-F-Ph N-CHPh

CO^e N-CMe₂ Br 7-Cl C0₂Me N-CHPh

C0₂Et N-CMe₂ Br 7-Cl C0₂Et N-CHPh

Me N-CMe₂ Br 7-Cl Me N-CHPh n-Pr N-CMe₂ Br 7-Cl n-Pr N-CHPh i-Pr N-CMe₂ Br 7-Cl i-Pr N-CHPh

4-F-Ph N-CMe₂ Br 7-Cl 4-F-Ph N-CHPh

C0₂Me N-CMe₂ Br 7-CF3 C0₂Me N-CHPh

C0₂Et N-CMe₂ Br 7-CF3 C0₂Et N-CHPh

₂ Br 7-CF3 Me N-CHPh

OCF3 7-CF3 n-Pr N-CMe₂ Br 7-CF3 n-Pr N-CHPh

OCF3 7-CF3 i-Pr N«CMe₂ Br 7-CF3 i-Pr N-CHPh

OCF3 7-CF3 4-F-Ph N-CMe₂ Br 7-CF3 4-F-Ph N-CHPh

CF3 6-F C0Me N-CHPh OCF3 6-F C0₂Me N-CHPh

CF3 6-F C0₂Et N-CHPh OCF3 6-F C0₂Et N-CHPh

CF₃ 6-F Me N-CHPh OCF3 6-F Me N-CHPh

CF₃ 6-F n-Pr N-CHPh OCF3 6-F n-Pr N-CHPh

CF₃ 6-F i-Pr N-CHPh OCF3 6-F i-Pr N-CHPh

CF3 6-F 4-F-Ph N-CHPh OCF3 6-F 4-F-Ph N-CHPh B¹ B^ B³ X B¹ B^ B³ X

CF₃ 7-F C0₂Me N-CHPh OCF₃ 7-F C0₂Me N-CHPh

CF₃ 7-F C0₂Et N-CHPh OCF₃ 7-F C0₂Et N-CHPh

CF3 7-F Me N-CHPh OCF3 7-F Me N-CHPh

CF₃ 7-F n-Pr N-CHPh OCF3 7-F n-Pr N-CHPh

CF₃ 7-F i-Pr N-CHPh OCF3 7-F i-Pr N-CHPh

CF₃ 7-F 4-F-Ph N-CHPh OCF3 7-F 4-F-Ph N-CHPh

CF₃ 7-Cl C0₂Me N-CHPh OCF3 7-Cl C0₂Me N-CHPh

CF₃ 7-Cl C0₂Et N-CHPh OCF3 7-Cl C0₂Et N-CHPh

CF3 7-Cl Me N-CHPh CF3 7-Cl Me N-CHPh

CF₃ 7-Cl n-Pr N-CHPh OCF₃ 7-Cl n-Pr N-CHPh

CF₃ 7-Cl i-Pr N-CHPh OCF₃ 7-Cl i-Pr N-CHPh

CF₃ 7-Cl 4-F-Ph N-CHPh OCF₃ 7-Cl 4-F-Ph N-CHPh

CF₃ 7-CF₃ C0₂Me N-CHPh OCF₃ 7-CF₃ C0₂Me N-CHPh

CF₃ 7-CF3 C0₂Et N-CHPh OCF₃ 7-CF₃ C0 Et N-CHPh

CF₃ 7"CF₃ Me N-CHPh OCF₃ 7-CF₃ Me N-CHPh

CF₃ 7-CF3 n-Pr N-CHPh OCF₃ 7-CF₃ n-Pr N-CHPh

CF₃ 7-CF3 i-Pr N-CHPh OCF₃ 7"CF₃ i-Pr N-CHPh

CF₃ 7-CF3 4-F-Ph N-CHPh OCF₃ 7-CF₃ 4-F-Ph N-CHPh

Br 6-F C0₂Me NH(CO)CF₃ CF₃ 6-F C0₂Me NH(CO)CF₃

Br 6-F C0₂Et NH(CO)CF₃ CF₃ 6-F C0 Et NH(CO)CF3

Br 6-F Me NH(CO)CF₃ CF3 6-F Me NH(CO)CF₃

Br 6-F n-Pr NH(CO)CF₃ CF₃ 6-F n-Pr NH(CO)CF₃

Br 6-F i-Pr NH(CO)CF₃ CF₃ 6-F i-Pr NH(CO)CF₃

Br 6-F 4-F-Ph NH(CO)CF₃ CF₃ 6-F 4-F-Ph NH(CO)CF₃

Br 7-F C0₂Me NH(CO)CF₃ CF₃ 7-F C0 Me NH(CO)CF3

Br 7-F C0₂Et NH(CO)CF₃ CF₃ 7-F C0₂Et NH(CO)CF3

Br 7-F Me NH(CO)CF₃ CF₃ 7-F Me NH(CO)CF₃

Br 7-F n-Pr NH(CO)CF₃ CF₃ 7-F n-Pr NH(CO)CF₃

Br 7-F i-Pr NH(CO)CF₃ C ₃ 7-F i-Pr NH(CO)CF₃

Br 7-F 4-F-Ph NH(CO)CF₃ CF₃ 7-F 4-F-Ph NH(CO)CF3

¹ B

^z B

³ X

Br 6-F C0₂Me OMe

Br 6-F C0₂Et OMe

Br 6-F Me OMe

Br 6-F n-Pr OMe

Br 6-F i-Pr OMe

Br 6-F 4-F-Ph OMe

Br 7-F C0₂Me OMe

Br 7-F C0 Et OMe

Br 7-F Me OMe

Br 7-F n-Pr OMe

Br 7-F i-Pr OMe

Br 7-F 4-F-Ph OMe

Br 7-Cl C0₂Me OMe

Br 7-Cl C0₂Et OMe

Br 7-Cl Me OMe

Br 7-Cl n-Pr OMe

Br 7-Cl i-Pr OMe

Br 7-Cl 4-F-Ph OMe

Br 7-CF3 C0₂Me OMe

Br 7-CF3 C0₂Et OMe

Br 7-CF3 Me OMe

Br 7-CF3 n-Pr OMe

Br 7-CF3 i-Pr OMe

Br 7-CF3 4-F-Ph OMe

OCF₃ 6-F C0₂Me OMe

OCF₃ 6-F C0₂Et OMe

OCF₃ 6-F Me OMe

OCF₃ 6-F n-Pr OMe OCF₃ 6-F i-Pr OMe OCF₃ 6-F 4-F-Ph OMe

¹ B^ B

³ X B B B

³ X

OCF₃ 7-F C0 Me OMe Br 7-F C0₂Me OCH₂Ph

OCF3 7-F C0₂Et OMe Br 7-F C0₂Et OCH₂Ph

OCF3 7-F Me OMe Br 7-F Me OCH Ph

OCF3 7-F n-Pr OMe Br 7-F n-Pr OCH₂Ph

OCF3 7-F i-Pr OMe Br 7-F i-Pr OCH₂Ph

OCF3 7-F 4-F-Ph OMe Br 7-F 4-F-Ph OCH₂Ph

OCF3 7-Cl C0₂Me OMe Br 7-Cl C0₂Me OCH₂Ph

OCF3 7-Cl C0₂Et OMe Br 7-Cl C0₂Et OCH₂Ph

OCF₃ 7-Cl Me OMe Br 7-Cl Me OCH₂Ph

OCF₃ 7-Cl n-Pr OMe Br 7-Cl n-Pr OCH₂Ph

OCF₃ 7-Cl i-Pr OMe Br 7-Cl i-Pr OCH₂Ph

OCF₃ 7-Cl 4-F-Ph OMe Br 7-Cl 4-F-Ph OCH₂Ph

OCF₃ 7-CF₃ C0₂Me OMe Br 7-CF3 C0 Me OCH₂Ph

OCF₃ 7-CF₃ C0₂Et OMe Br 7-CF3 C0₂Et OCH₂Ph

OCF₃ 7-CF₃ Me OMe Br 7-CF3 Me OCH₂Ph

OCF3 7-C 3 n-Pr OMe Br 7-CF3 n-Pr OCH₂Ph

0CF₃ 7-CF3 i-Pr OMe Br 7-CF3 i-Pr OCH₂Ph

OCF₃ 7-CF3 4-F-Ph OMe Br 7-CF3 4-F-Ph OCH₂Ph

CF₃ 6-F C0 Me OCH₂Ph OCF3 6-F C0₂Me OCH₂Ph

CF₃ 6-F C0₂Et OCH₂Ph OCF3 6-F C0₂Et OCH₂Ph

CF₃ 6-F Me OCH₂Ph OCF3 6-F Me OCH₂Ph

CF₃ 6-F n-Pr OCH₂Ph OCF3 6-F n-Pr OCH₂Ph

CF₃ 6-F i-Pr OCH₂Ph OCF3 6-F i-Pr OCH₂Ph

CF₃ 6-F 4-F-Ph OCH₂Ph OCF3 6-F 4-F-Ph OCH₂Ph

CF₃ 7-F C0₂Me OCH₂Ph OCF3 7-F C0 Me OCH₂Ph

CF₃ 7-F C0₂Et OCH Ph OCF3 7-F C0₂Et OCH₂Ph

CF₃ 7-F Me OCH₂Ph OCF3 7-F Me OCH Ph

CF₃ 7-F n-Pr OCH₂Ph OCF3 7-F n-Pr OCH Ph

CF₃ 7-F i-Pr OCH₂Ph OCF3 7-F i-Pr OCH₂Ph

CF₃ 7-F 4-F-Ph OCH₂Ph OCF3 7-F 4-F-Ph OCH₂Ph

¹ B B

³ X B

^α B^ B

³

CF3 7-CF3 C0₂Me NHS0₂NH₂ CF3 7-CF3 C0₂Me NH(4-Me0-Ph)

OCF3 7-CF3 C0₂Me NHS0₂NH₂ OCF3 7-CF3 C0₂Me NH(4-MeO-Ph)

CF3 7-Cl i-Pr NHS0₂NH₂ CF₃ 7-Cl i-Pr NH(4-MeO-Ph)

OCF3 7-Cl i-Pr NHS0 NH₂ OCF3 7-Cl i-Pr NH(4-MeO-Ph)

CF₃ 7-CF3 4-F-Ph NHS0₂NH CF₃ 7-CF3 4-F-Ph NH(4-MeO-Ph)

OCF3 7-CF3 4-F-Ph NHS0₂NH₂ OCF3 7-CF3 4-F-Ph NH(4-MeO-Ph)

CF₃ 7-CF3 C0₂Me NHS0₂NHPh CF3 7-CF3 C0₂Me NHCH OCH

OCF3 7-CF3 C0₂Me NHS0₂NHPh OCF3 7-CF3 C0₂Me NHCH C_CH

CF₃ 7-Cl i-Pr NHS0₂NHPh CF3 7-Cl i-Pr NHCH C_CH

OCF3 7-Cl i-Pr NHS0₂NHPh OCF3 7-Cl i-Pr NHCH₂C_CH

CF₃ 7-CF3 4-F-Ph NHS0₂NHPh CF3 7-CF3 4-F-Ph NHCH₂OCH

OCF 7-CF3 4-F-Ph NHS0₂NHPh OCF-a 7-CF3 4-F-Ph NHCH₂C_CH

¹ B

³ X B

¹ B^ B

³ X

OCF₃ 7-F C0 Me NH₂ Br 7-F C0₂Me NHMe

OCF3 7-F C0₂Et NH₂ Br 7-F C0₂Et NHMe

OCF3 7-F Me NH₂ Br 7-F Me NHMe

OCF3 7-F n-Pr NH₂ Br 7-F n-Pr NHMe

OCF3 7-F i-Pr NH₂ Br 7-F i-Pr NHMe

OCF₃ 7-F 4-F-Ph NH₂ Br 7-F 4-F-Ph NHMe

OCF₃ 7-Cl C0 Me NH₂ Br 7-Cl C0₂Me NHMe

OCF₃ 7-Cl C0₂Et NH₂ Br 7-Cl C0₂Et NHMe

OCF₃ 7-Cl Me NH₂ Br 7-Cl Me NHMe

0CF₃ 7-Cl n-Pr NH₂ Br 7-Cl n-Pr , NHMe I

OCF₃ 7-Cl i-Pr NH₂ Br 7-Cl i-Pr NHMe

OCF₃ 7-Cl 4-F-Ph NH₂ Br 7-Cl 4-F-Ph NHMe

OCF₃ 7-CF₃ C0₂Me NH₂ Br 7-CF₃ C0₂Me NHMe

OCF₃ 7-CF₃ C0₂Et NH₂ Br 7-CF₃ C0₂Et NHMe

0CF₃ 7-CF₃ Me NH₂ Br 7-CF₃ Me NHMe

OCF₃ 7-CF₃ n-Pr NH₂ Br 7-CF₃ n-Pr NHMe

OCF₃ 7-CF₃ i-Pr NH₂ Br 7-CF₃ i-Pr NHMe

OCF₃ 7-CF₃ 4-F-Ph NH₂ Br 7-CF₃ 4-F-Ph NHMe

CF₃ 6-F C0₂Me NHMe OCF₃ 6-F C0₂Me NHMe

CF₃ 6-F C0₂Et NHMe OCF₃ 6-F C0₂Et NHMe

CF₃ 6-F Me NHMe OCF₃ 6-F Me NHMe

CF₃ 6-F n-Pr NHMe OCF₃ 6-F n-Pr NHMe

CF₃ 6-F i-Pr NHMe OCF₃ 6-F i-Pr NHMe

CF₃ 6-F 4-F-Ph NHMe OCF₃ 6-F 4-F-Ph NHMe

CF₃ 7-F C0₂Me NHMe OCF₃ 7-F C0₂Me NHMe CF₃ 7-F C0₂Et NHMe OCF₃ 7-F C0₂Et NHMe CF3 7-F Me NHMe OCF₃ 7-F Me NHMe CF3 7-F n-Pr NHMe OCF₃ 7-F n-Pr NHMe CF3 7-F i-Pr NHMe OCF₃ 7-F i-Pr NHMe CF₃ 7-F 4-F-Ph NHMe OCF₃ 7-F 4-F-Ph NHMe

¹ B B

³ X

CF₃ 7-Cl C0₂Me NHMe

CF₃ 7-Cl C0₂Et NHMe

CF₃ 7-Cl Me NHMe

CF₃ 7-Cl n-Pr NHMe

CF₃ 7-Cl i-Pr NHMe

CF₃ 7-Cl 4-F-Ph NHMe

CF₃ 7-CF3 C0₂Me NHMe

CF₃ 7-CF3 C0₂Et NHMe

CF₃ 7-CF3 Me NHMe

CF₃ 7-CF3 n-Pr NHMe

CF₃ 7-CF3 i-Pr NHMe

C ₃ 7-CF3 4-F-Ph NHMe

Br 6-F C0₂Me NHCHO

Br 6-F C0₂Et NHCHO

Br 6-F Me NHCHO

Br 6-F n-Pr NHCHO

Br 6-F i-Pr NHCHO

Br 6-F 4-F-Ph NHCHO

Br 7-F C0₂Me NHCHO

Br 7-F C0₂Et NHCHO

Br 7-F Me NHCHO

Br 7-F n-Pr NHCHO

Br 7-F i-Pr NHCHO

Br 7-F 4-F-Ph NHCHO

Br 7-Cl C0₂Me NHCHO

Br 7-Cl C0₂Et NHCHO

Br 7-Cl Me NHCHO

Br 7-Cl n-Pr NHCHO

Br 7-Cl i-Pr NHCHO

Br 7-Cl 4-F-Ph NHCHO

³ X B

¹ B* B

³ X

Br 7-CF3 C0₂Me NHCHO CF3 7-CF3 CO^e NHCHO

Br 7-CF3 C0₂Et NHCHO CF₃ 7-CF3 C0₂Et NHCHO

Br 7-CF3 NHCHO CF3 7-CF₃ Me NHCHO

Br 7-CF3 n-Pr NHCHO CF3 7-CF3 n-Pr NHCHO

Br 7-CF3 i-Pr NHCHO CF₃ 7-CF3 i-Pr NHCHO

Br 7-CF3 4-F-Ph NHCHO CF3 7-CF3 4-F-Ph NHCHO

OCF₃ 6-F C0₂Me NHCHO Br 6-F C0₂Me NH(CO)Me

OCF3 6-F C0₂Et NHCHO Br 6-F C0₂Et NH(CO)Me

OCF3 6-F Me NHCHO Br 6-F M© NH(CO)Me

OCF3 6-F n-Pr NHCHO Br 6-F n-Pr NH(CO)Me

OCF3 6-F i-Pr NHCHO Br 6-F i-Pr NH(CO)Me

OCF3 6-F 4-F-Ph NHCHO Br 6-F 4-F-Ph NH(CO)Me

OCF3 7-F C0₂Me NHCHO Br 7-F CO^e NH(CO)Me

OCF3 7-F C0₂Et NHCHO Br 7-F C0 Et NH(CO)Me

OCF3 7-F Me NHCHO Br 7-F Me NH(CO)Me

OCF3 7-F n-Pr NHCHO Br 7-F n-Pr NH(CO)Me

OCF3 7-F i-Pr NHCHO Br 7-F i-Pr NH(CO)Me

OCF3 7-F 4-F-Ph NHCHO Br 7-F 4-F-Ph NH(CO)Me

OCF3 7-Cl C0₂Me NHCHO Br 7-Cl C0₂Me NH(CO)Me

OCF3 7-Cl C0₂Et NHCHO Br 7-Cl C0₂Et NH(CO)Me

OCF3 7-Cl Me NHCHO Br 7-Cl Me NH(CO)Me

OCF3 7-Cl n-Pr NHCHO Br 7-Cl n-Pr NH(CO)Me

OCF3 7-Cl i-Pr NHCHO Br 7-Cl i-Pr NH(CO)Me

OCF3 7-Cl 4-F-Ph NHCHO Br 7-Cl 4-F-Ph NH(CO)Me

OCF3 7-CF3 C0₂Me NHCHO Br 7-CF3 C0₂Me NH(CO)Me

OCF3 7-CF3 C0₂Et NHCHO Br 7-CF3 C0₂Et NH(CO)Me

OCF3 7-CF3 Me NHCHO Br 7-CF3 Me NH(CO)Me

OCF3 7-CF3 n-Pr NHCHO Br 7-CF3 n-Pr NH(CO)Me

OCF3 7-CF3 i-Pr NHCHO Br 7-CF3 i-Pr NH(CO)Me

OCF3 7-CF3 4-F-Ph NHCHO Br 7-CF3 4-F-Ph NH(CO)Me

¹ B

³ X B

^A B^ B

³ X

OCF₃ 7-Cl C0₂Me OMe Br 7-Cl C0₂Me N-CHPh

OCF3 7-Cl C0₂Et OMe Br 7-Cl C0₂Et N-CHPh

OCF3 7-Cl Me OMe Br 7-Cl Me N-CHPh

OCF3 7-Cl n-Pr OMe Br 7-Cl n-Pr N-CHPh

OCF3 7-Cl i-Pr OMe Br 7-Cl i-Pr N-CHPh

0CF₃ 7-Cl 4-F-Ph OMe Br 7-Cl 4-F-Ph N-CHPh

OCF₃ 7-CF₃ C0 Me OMe Br 7-CF₃ CO_jjMe N-CHPh

OCF₃ 7-CF₃ C0₂Et OMe Br 7-CF3 C0₂Et N-CHPh

OCF₃ 7-CF₃ Me OMe Br 7-CF3 Me N-CHPh

OCF₃ 7-CF₃ n-Pr OMe Br 7-CF3 n-Pr N-CHPh

OCF₃ 7-CF₃ i-Pr OMe Br 7-CF3 i-Pr N-CHPh

OCF₃ 7-CF₃ 4-F-Ph OMe Br 7-CF3 4-F-Ph N-CHPh

CF₃ 6-F C0₂Me N-CHPh OCF₃ 6-F C0₂Me N-CHPh

CF₃ 6-F C0 Et N-CHPh OCF₃ 6-F C0 Et N-CHPh

CF₃ 6-F Me N-CHPh OCF₃ 6-F Me N-CHPh

CF₃ 6-F n-Pr N-CHPh OCF₃ 6-F n-Pr N-CHPh

CF₃ 6-F i-Pr N-CHPh OCF₃ 6-F i-Pr N-CHPh

CF₃ 6-F 4-F-Ph N-CHPh OCF₃ 6-F 4-F-Ph N-CHPh

CF₃ 7-F C0₂Me N-CHPh OCF₃ 7-F C0₂Me N-CHPh

C ₃ 7-F C0₂Et N-CHPh OCF₃ 7-F C0₂Et N-CHPh CF₃ 7-F Me N-CHPh OCF₃ 7-F Me N-CHPh CF₃ 7-F n-Pr N-CHPh OCF₃ 7-F n-Pr N-CHPh

CF₃ 7-F i-Pr N-CHPh OCF₃ 7-F i-Pr N-CHPh CF₃ 7-F 4-F-Ph N-CHPh OCF₃ 7-F 4-F-Ph N-CHPh CF₃ 7-Cl C0₂Me N-CHPh OCF₃ 7-Cl C0₂Me N-CHPh CF₃ 7-Cl C0₂Et N-CHPh OCF₃ 7-Cl C0₂Et N-CHPh CF₃ 7-Cl Me N-CHPh OCF₃ 7-Cl Me N-CHPh CF₃ 7-Cl n-Pr N-CHPh OCF₃ 7-Cl n-Pr N-CHPh CF₃ 7-Cl i-Pr N-CHPh OCF₃ 7-Cl i-Pr N-CHPh CF₃ 7-Cl 4-F-Ph N-CHPh OCF₃ 7-Cl 4-F-Ph N-CHPh

¹ B B

³ X B

¹ # B-

³ X

CF₃ 7-Cl C0₂Me Et CO^e Et

CF₃ 7-Cl C0₂Et Et C0₂Et Et

CF₃ 7-Cl Me Et Me Et

CF3 7-Cl n-Pr Et n-Pr Et

CF₃ 7-Cl i-Pr Et i-Pr Et

C ₃ 7-Cl 4-F-Ph Et 4-F-Ph Et CF₃ 7-CF3 C0₂Me Et C0₂Me Et CF₃ 7-CF3 C0₂Et Et C0₂Et Et CF₃ 7-CF3 Me Et Me Et CF₃ 7-CF3 n-Pr Et n-Pr f.t CF₃ 7-CF3 i-Pr Et i-Pr Et

CF₃ 7-CF3 4-F-Ph Et 4-F-Ph Et

Br 6-F C0₂Me -CH₂OCH₃

₂OCH

₃

Br 6-F C0₂Et -CH₂OCi_3 CF3 6-F C0₂Et -CH₂OCH₃

Br 6-F Me -CH₂OCH₃ CF3 6-F Me -CH₂OCH₃

Br 6-F n-Pr -CH₂OCH₃ CF3 6-F n-Pr -CH₂OCH₃

Br 6-F i-Pr -CH₂OCH₃ CF3 6-F i-Pr —CH₂OCH₃

Br 6-F 4-F-Ph -CH₂OCH₃ CF3 6-F 4-F-Ph -CH₂OCH₃

Br 7-F C0₂Me -CH₂OCH₃ CF3 7-F C0Me -CH₂OCH₃

Br 7-F C0₂Et -CH₂OCH₃ CF3 7-F C0₂Et -CH₂OCH₃

Br 7-F Me -CH₂OCH₃ CF₃ 7-F Me -CH₂OCH₃

Br 7-F n-Pr -CH₂OCH₃ CF₃ 7-F n-Pr -CH₂OCH₃

Br 7-F i-Pr -CH₂OCH₃ CF₃ 7-F i-Pr -CH₂OCH₃

Br 7-F 4-F-Ph -CH₂OCH₃ CF₃ 7-F 4-F-Ph -CH₂OCH₃

Br 7-Cl C0₂Me -CH₂OCH₃ CF₃ 7-Cl C0₂Me -CH₂OCH₃

Br 7-Cl C0₂Et -CH₂OCH₃ CF₃ 7-Cl C0₂Et -CH₂OCH₃

Br 7-Cl Me -CH₂OCH₃ CF₃ 7-Cl Me -CH₂OCH₃

Br 7-Cl n-Pr -CH₂OCH₃ CF₃ 7-Cl n-Pr -CH₂OCH₃

Br 7-Cl i-Pr -CH₂OCH₃ CF₃ 7-Cl i-Pr -CH₂OCH₃

Br 7-Cl 4-F-Ph -CH₂OCH₃ CF₃ 7-Cl 4-F-Ph —CH₂OCH₃

8 Q Q O Q O O Q Q Q O O Q Q O O O Q Q Q O Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω Ω O Ω Ω Ω co co co co co co co oo oo co co co co oo co oo co oo oo oo c

-4 s4 sJ -4 -4 sj _J ^l -j •4 s ~ •sl s^j sJ -4 -sl -sl Ol OI I I I I I I I I I I I I I I I I I I I I Ω Ω Ω Ω Ω Ω O Ω Ω Ω Ω Ω tn tΛ tΛ tn ππ tn In i

. .. . . . . H H H H co co oo co co oo

I I I I I I I I I I I I I I I I I a .- Oa Ωa Ωa Ωa Ωa Ωa Ωa Ωa Ωa Ωa Ωa Ωa Ω O Ω Ω Ω Ω Ω

M M M M M M M M M M M M M Ma Ma Ma Ma Ma Ma Ma

8 a 8a 8a 8a 8a 88 88 8 co co co co co cao ca 8 o ca 8 o ca 8 o ca 8 o ωa 8 ca 8 888 8 o cao cao ωa oao cao cao cao cao

I I I I I I I I I I I I I I I I I I I I Oa Ωa Ωa Ωa Ωa Oa Ωa Ωa Ω Ω Ω Ω Ω

M M M M M M M M Ma Ma Ω Ma Ma Ω Ma Ω Ω Ω Ω Ω Ma Ma Ma Ma Ma Ma Ma

888 a 8 a 8888 a 88 a 8 a 88 a 88 a 8 a 88 a 88 a

B¹ B^ B^J X ¹ B B³ X

Br 7-CF3 C0₂Me -CH₂0_CH CF3 7-CF3 CO^e -CH₂C_CH

Br 7-C 3 C0₂Et -CH₂C_CH CF3 7-CF3 C0₂Et -CH₂C_CH

Br 7-CF3 Me -CH₂0_CH CF3 7-CF3 Me -CH₂C_CH

Br 7-CF3 n-Pr -CH₂C_CH CF3 7-CF3 n-Pr -CH₂0_CH

Br 7-CF3 Pr -CH₂C_CH CF3 7-CF3 i-Pr -CH₂0_CH

Br 7-CF3 4-F-Ph -CH OCH CF3 7-CF3 4-F-Ph -CH C_CH

OCF₃ 6-F C0₂Me -CH₂Q-CH Br 6-F C0₂Me -CH₂CH=CH₂

OCF3 6-F C0 Et -CH₂*CH Br 6-F C0₂Et -CH₂CH=CH₂

OCF3 6-F Me -CH C-CH Br 6-F Me -CH₂CH_CH₂

OCF3 6-F n-Pr -CH₂C_CH Br 6-F n-Pr -CH₂CH=CH₂

OCF3 6-F Pr -CH₂C_CH Br 6-F Pr -CH₂CH=CH₂

OCF3 6-F 4-F-Ph -CH₂C_CH Br 6-F 4-F-Ph -CH₂CH=CH₂

OCF3 7-F C0₂Me -CH₂OCH Br 7-F C0₂Me —CH₂CH— H₂

OCF3 7-F C0₂Et -CH₂C_CH Br 7-F C0₂Et -CH₂CH=CH₂

OCF3 7-F Me -CH₂0_CH Br 7-F Me -CH₂CH=CH₂

OCF3 7-F n-Pr -CH₂C«CH Br 7-F n-Pr -CH₂CH=CH

OCF₃ 7-F Pr -CH₂C-CH Br 7-F Pr -CH₂CH=CH₂

OCF₃ 7-F 4-F-Ph -CH₂C_CH Br 7-F 4-F-Ph -CH₂CH=CH₂

CF₃ 7-F C0₂Me -CH₂C_CH OCF3 7-Cl C0₂Me -CH₂C_CH

CF₃ 7-F C0 Et -CH₂OCH OCF3 7-Cl C0₂Et -CH₂C_CH

CF₃ 7-F Me -CH₂C_CH OCF3 7-Cl Me -CH₂C-CH

CF₃ 7-F n-Pr -CH₂C_CH OCF3 7-Cl n-Pr -CH₂C_CH

CF₃ 7-F i-Pr -CH₂C_CH OCF3 7-Cl Pr -CH₂C«CH

CF₃ 7-F 4-F-Ph -CH₂C_CH OCF3 7-Cl 4-F-Ph -CH₂C_CH

CF₃ 7-Cl CO^e -CH₂CβCH OCF3 7-CF3 C0₂Me -CH₂CβCH

CF3 7-Cl C0₂Et -CH C_CH OCF3 7-CF3 C0₂Et -CH C_CH

CF3 7-Cl Me -CH₂C_CH OCF3 7-CF3 Me -CH₂OCH

CF3 7-Cl n-Pr -CH₂C_CH OCF3 7-CF3 n-Pr -CH CβCH

CF3 7-Cl i-Pr -CH₂C_CH OCF3 7-CF3 Pr -CH₂C_CH

CF3 7-Cl 4-F-Ph -CH₂C_CH OCF3 7-CF3 4-F-Ph -CH₂C*CH B¹ B^ B³ B¹ B^ B³

CF₃ 6-F C0₂Me -CH₂CH=CH₂ OCF₃ 6-F C0₂Me -CH₂CH=CH₂

CF₃ 6-F C0₂Et -CH₂CH=CH OCF₃ 6-F C0₂Et -CH₂CH=CH₂

CF₃ 6-F Me -CH₂CH=CH₂ OCF₃ 6-F Me -CH₂CH=CH₂

CF₃ 6-F n-Pr -CH₂CH=CH₂ OCF₃ 6-F n-Pr -CH₂CH=CH₂

CF₃ 6-F Pr -CH CH=CH₂ OCF₃ 6-F Pr -CH₂CH=CH₂

CF₃ 6-F 4-F-Ph -CH₂CH=CH₂ OCF₃ 6-F 4-F-Ph -CH₂CH=CH₂ ^F3 7-F C0₂Me -CH₂CH=CH₂ OCF₃ 7-F C0₂Me -CH CH=CH₂ CF₃ 7-F C0 Et -CH₂CH-CH₂ OCF₃ 7-F CO_zEt -CH₂CH=CH₂

CF₃ 7-F Me -CH₂CH=CH₂ OCF3 7-F Me -CH₂CH=CH₂

CF₃ 7-F n-Pr -CH CH=CH₂ OCF3 7-F n-Pr CH₂CH=CH₂

CF₃ 7-F Pr -CH₂CH=CH₂ OCF3 7-F Pr -CH₂CH=CH₂

C ₃ 7-F 4-F-Ph -CH₂CH=CH₂ OCF3 7-F 4-F-Ph -CH₂CH=CH₂

CF3 7-Cl Cθ₂Me -CH CH=CH₂ OCF3 7-Cl C0₂Me -CH₂CH=CH₂

CF₃ 7-Cl C0₂Et -CH₂CH=CH₂ OCF3 7-Cl C0₂Et -CH₂CH=CH₂

CF₃ 7-Cl Me -CH₂CH=CH₂ OCF3 7-Cl Me -CH₂CH=CH₂

CF₃ 7-Cl n-Pr -CH₂CH=CH₂ OCF3 7-Cl n-Pr —CH₂CH—CH₂

C ₃ 7-Cl Pr -CH₂CH=CH₂ OCF3 7-Cl Pr -CH₂CH=CH₂

CF₃ 7-Cl 4-F-Ph -CH₂CH=CH₂ OCF3 7-Cl 4-F-Ph -CH₂CH=CH₂

Br 7-Cl C0₂Me -CH₂CH-CH₂ CF₃ 7-CF3 C0₂Me —CH₂CH_CH₂

Br 7-Cl C0₂Et -CH₂CH=CH₂ CF₃ 7-CF3 C0₂Et -CH₂CH=CH₂

Br 7-Cl Me -CH₂CH_CH₂ CF3 7-CF3 Me —CH₂CH—CH₂

Br 7-Cl n-Pr -CH₂CH=CH₂ CF3 7-CF3 n-Pr —CH₂CH_CH₂

Br 7-Cl Pr -CH CH=CH₂ CF₃ 7-CF3 Pr -CH₂CH_CH₂

Br 7-Cl 4-F-Ph -CH₂CH=CH₂ CF₃ 7-CF3 4-F-Ph -CH₂CH=CH₂

Br 7-CF₃ C0₂Me -CH₂CH=CH₂ OCF3 7-CF3 C0₂Me -CH₂CH_CH₂

Br 7-CF₃ C0₂Et -CH₂CH=CH₂ OCF3 7-CF3 C0₂Et —CH₂CH—CH₂

Br 7"CF₃ Me -CH CH=CH₂ OCF3 7-CF3 Me -CH CH=CH₂

Br 7-CF₃ n-Pr -CH₂CH=CH₂ OCF3 7-CF3 n-Pr -CH₂CH=CH

Br 7-CF₃ Pr -CH₂CH=CH₂ OCF3 7-CF3 Pr -CH₂CH=CH₂

Br 7-CF₃ 4-F-Ph -CH₂CH=CH₂ OCF3 7-CF3 4-F-Ph -CH₂CH=CH₂

^x ^ B

^J X B B^ B

³ X

Br 6-F C0₂Me NHMe CF₃ 7-Cl C0₂Me NHMe

Br 6-F C0₂Et NHMe CF₃ 7-Cl C0 Et NHMe

Br 6-F i-Pr NHMe CF₃ 7-Cl i-Pr NHMe

Br 6-F Me NHMe CF₃ 7-Cl Me NHMe

Br 6-F 4-F-Ph NHMe CF₃ 7-CΪ 4-F-Ph NHMe

Br 7-F C0₂Me NHMe CF₃ 7-CF₃ C0 Me NHMe

Br 7-F C0₂Et NHMe CF₃ 7-CF₃ C0₂Et NHMe

Br 7-F i-Pr NHMe CF₃ 7-CF₃ i-Pr NHMe

Br 7-F Me NHMe CF₃ 7-CF₃ Me NHMe

Br 7-F 4-F-Ph NHMe CF₃ 7-CF₃ 4-F-Ph NHMe

Br 7-Cl C0₂Me NHMe OCF₃ 6-F C0₂Me NHMe

Br 7-Cl C0 Et NHMe OCF₃ 6-F C0₂Et NHMe

Br 7-Cl i-Pr NHMe OCF₃ 6-F i-Pr NHMe

Br 7-Cl Me NHMe OCF₃ 6-F Me NHMe

Br 7-Cl 4-F-Ph NHMe OCF₃ 6-F 4-F-Ph NHMe

Br 7-CF₃ C0₂Me NHMe OCF₃ 7-F C0 Me NHMe

Br 7-CF₃ C0₂Et NHMe OCF₃ 7-F C0₂Et NHMe

Br 7-CF₃ i-Pr NHMe OCF₃ 7-F i-Pr NHMe

Br 7-CF₃ Me NHMe OCF₃ 7-F Me NHMe

Br 7~CF₃ 4-F-Ph NHMe OCF₃ 7-F 4-F-Ph NHMe

CF₃ 6-F C0₂Me NHMe OCF₃ 7-Cl C0 Me NHMe

CF₃ 6-F C0₂Et NHMe OCF₃ 7-Cl C0₂Et NHMe

CF₃ 6-F i-Pr NHMe OCF₃ 7-Cl i-Pr NHMe

CF₃ 6-F Me NHMe OCF₃ 7-Cl Me NHMe

CF₃ 6-F 4-F-Ph NHMe OCF₃ 7-Cl 4-F-Ph NHMe

CF₃ 7-F C0₂Me NHMe OCF₃ 7-CF₃ C0₂Me NHMe

CF₃ 7-F C0₂Et NHMe OCF₃ 7-CF₃ C0₂Et NHMe

CF₃ 7-F i-Pr NHMe OCF₃ 7-CF₃ i-Pr NHMe

CF₃ 7-F Me NHMe OCF₃ 7"CF₃ Me NHMe

C ₃ 7-F 4-F-Ph NHMe OCF₃ 7-CF₃ 4-F-Ph NHMe

^<= B

^J X B

¹ B^ B

⁵ X

Br 6-F C0₂Me NH.CO_.Me CF3 7-Cl C0₂Me NH(CO)Me

Br 6-F C0₂Et NH(CO)Me CF₃ 7-Cl C0₂Et NH(CO)Me

Br 6-F i-Pr NH(CO)Me CF₃ 7-Cl i-Pr NH(C )Me

Br 6-F Me NH(CO)Me CF₃ 7-Cl Me NH.CO.Me

Br 6-F 4-F-Ph NH(CO)Me CF₃ 7-Cl 4-F-Ph NH.CO.Me

Br 7-F C0₂Me NH(CO)Me CF3 7-CF3 C0₂Me NH.CO_.Me

Br 7-F C0₂Et NH(CO)Me CF₃ 7-CF3 C0₂Et NH(CO) e

Br 7-F i-Pr NH(CO)Me CF3 7-CF3 i-Pr NH(CO)Me

Br 7-F Me NH(CO)Me CF₃ 7-CF3 Me NH.CO.Me

Br 7-F 4-F-Ph NH(CO)Me CF3 7-CF3 4-F-Ph NH.CO.Me

Br 7-Cl C0₂Me NH(CO)Me OCF3 6-F C0₂Me NH(CO)Me

Br 7-Cl C0₂Et NH(CO)Me OCF3 6-F C0₂Et NH(CO)Me

Br 7-Cl i-Pr NH(CO)Me OCF3 6-F i-Pr NH(CO)Me

Br 7-Cl Me NH(CO)Me OCF3 6-F Me NH(CO)Me

Br 7-Cl 4-F-Ph NH(CO)Me OCF3 6-F 4-F-Ph NH(CO)Me

Br 7-CF3 C0₂Me NH(CO)Me OCF3 7-F C0₂Me NH(CO)Me

Br 7-CF3 C0₂Et NH(CO)Me OCF3 7-F C0₂Et NH(CO)Me

Br 7-CF3 i-Pr NH.CO.Me OCF3 7-F i-Pr NH.CO.Me

Br 7-CF3 Me NH(CO)Me OCF3 7-F Me NH.CO.Me

Br 7-CF3 4-F-Ph NH(CO)Me OCF3 7-F 4-F-Ph NH(CO)Me

C ₃ 6-F C0₂Me NH(CO)Me OCF3 7-Cl C0₂Me NH(CO)Me CF₃ 6-F C0 Et NH(CO)Me OCF3 7-Cl C0₂Et NH(CO)Me

C ₃ 6-F i-Pr NH(CO)Me OCF3 7-Cl i-Pr NH(CO)Me CF₃ 6-F Me NH(CO)Me OCF3 7-Cl Me NH(CO)Me

CF₃ 6-F 4-F-Ph NH(CO)Me OCF3 7-Cl 4-F-Ph NH(CO)Me CF₃ 7-F C0₂Me NH(CO)Me OCF3 7-CF3 C0₂Me NH(CO)Me CF₃ 7-F C0₂Et NH(CO)Me OCF3 7-CF3 C0₂Et NH(CO)Me CF₃ 7-F i-Pr NH(CO)Me OCF3 7-CF3 i-Pr NH(CO)Me

CF₃ 7-F Me NH(CO)Me OCF3 7-CF3 Me NH(CO)Me CF₃ 7-F 4-F-Ph NH(CO)Me OCF3 7-CF3 4-F-Ph NH(CO)Me B^x B B³ X B¹ B^z B³ X

Br 6-F C0₂Me NH(CO)NHMe C 3 7-Cl C0₂Me NH(CO)NHMe

Br 6-F C0₂Et NH(CO)NHMe CF3 7-Cl C0₂Et NH(CO)NHMe

Br 6-F i-Pr NH(CO) HMe CF3 7-Cl i-Pr NH(CO)NHMe

Br 6-F Me NH(CO)NHMe CF3 7-Cl Me NH(CO)NHMe

Br 6-F 4-F-Ph NH(CO)NHMe CF3 7-Cl 4-F-Ph NH(CO)NHMe

Br 7-F CO_jjMe NH(CO)NHMe CF3 7-CF3 O0Me NH(CO)NHMe

Br 7-F C0₂Et NH(CO)NHMe CF3 7-CF3 C0 Et NH(CO)NHMe

Br 7-F i-Pr NH(CO)NHMe CF₃ 7-CF3 i-Pr NH(CO)NHMe

Br 7-F Me NH(CO)NHMe CF3 7-CF3 Me NH(CO)NHMe

Br 7-F 4-F-Ph NH(CO)NHMe CF3 7-CF3 4-F-Ph NH(CO)NHMe

Br 7-Cl C0₂Me NH(CO)NHMe OCF₃ 6-F C0₂Me NH(CO)NHMe

Br 7-Cl C0₂Et NH(CO) HMe OCF₃ 6-F C0₂Et NH(CO)NHMe

Br 7-Cl i-Pr NH(CO)NHMe OCF₃ 6-F i-Pr NH(CO)NHMe

Br 7-Cl Me NH(CO)NHMe OCF₃ 6-F Me NH(CO)NHMe

Br 7-Cl 4-F-Ph NH(CO)NHMe OCF₃ 6-F 4-F-Ph NH(CO)NHMe

Br 7-CF3 C0₂Me NH(CO)NHMe OCF₃ 7-F CO^e NH(CO)NHMe

Br 7-CF3 C0₂Et NH(CO)NHMe OCF₃ 7-F C0₂Et NH(CO)NHMe

Br 7-CF3 i-Pr NH(CO) HMe OCF₃ 7-F i-Pr NH(CO)NHMe

Br 7-CF3 Me NH(CO)NHMe OCF₃ 7-F Me NH(CO)NHMe

Br 7-CF3 4-F-Ph NH(CO)NHMe OCF₃ 7-F 4-F-Ph NH(CO)NHMe

CF₃ 6-F C0₂Me NH(CO)NHMe OCF₃ 7-Cl C0₂Me NH(CO)NHMe C ₃ 6-F C0₂Et NH(CO)NHMe OCF₃ 7-Cl C0₂Et NH(CO)NHMe CF₃ 6-F i-Pr NH(CO)NHMe OCF₃ 7-Cl i-Pr NH(CO)NHMe CF₃ 6-F Me NH(CO)NHMe OCF₃ 7-Cl Me NH(CO)NHMe CF₃ 6-F 4-F-Ph NH(CO)NHMe OCF₃ 7-Cl 4-F-Ph NH(CO)NHMe CF₃ 7-F CO^e NH(CO)NHMe OCF₃ 7-CF3 CO«>Me NH(CO)NHMe CF₃ 7-F C0₂Et NH(CO)NHMe OCF3 7-CF3 C0₂Et NH(CO)NHMe CF3 7-F i-Pr NH(CO)NHMe OCF3 7-CF3 i-Pr NH(CO)NHMe CF₃ 7-F Me NH(CO) HMe OCF3 7-CF3 Me NH(CO)NHMe CF₃ 7-F 4-F-Ph NH(CO)NHMe OCF3 7-CF3 4-F-Ph NH(CO)NHMe B B^<= B^J X B¹ B B^J X

Br 6-F C0₂Me N-CH₂ C ₃ 7-Cl C0₂Me N-CH₂

Br 6-F C0₂Et N-CH₂ CF₃ 7-Cl C0₂Et N-CH₂

Br 6-F i-Pr N—CH₂ CF₃ 7-Cl i-Pr N-CH₂

Br 6-F Me N—CH₂ CF₃ 7-Cl Me N"CH₂

Br 6-F 4-F-Ph N*"CH₂ CF₃ 7-Cl 4-F-Ph N« :H₂

Br 7-F C0₂Me N_™CH CF₃ 7-CF3 C0 Me N-CH₂

Br 7-F C0 Et N_CH₂ CF₃ 7-CF3 C0 Et N-CH₂

Br 7-F i-Pr N-CH₂ CF₃ 7-CF3 i-Pr N-CH₂

Br 7-F Me N-CH₂ CF₃ 7-CF3 Me N-CH₂

Br 7-F 4-F-Ph N-CH₂ CF₃ 7-CF3 4-F-Ph N-CH

Br 7-Cl C0₂Me N-CH₂ OCF₃ 6-F C0₂Me N-CH₂

Br 7-Cl C0₂Et N-CH₂ OCF3 6-F C0₂Et N-CH₂

Br 7-Cl i-Pr N-CH₂ OCF3 6-F i-Pr N-CH₂

Br 7-Cl Me N-CH₂ OCF3 6-F Me N-CH₂

Br 7-Cl 4-F-Ph N-CH₂ OCF3 6-F 4-F-Ph N-CH

Br 7~CF₃ C0₂Me N-CH₂ OCF3 7-F C0₂Me N-CH₂

Br 7-CF₃ C0₂Et N-CH OCF3 7-F C0₂Et N-CH₂

Br 7-CF₃ i-Pr N-CH₂ OCF3 7-F i-Pr N-CH₂

Br 7-CF₃ Me N-CH₂ OCF3 7-F Me N-CH

Br 7"CF₃ 4-F-Ph N-CH₂ OCF3 7-F 4-F-Ph N-CH₂

CF₃ 6-F C0₂Me N-CH₂ OCF3 7-Cl C0₂Me N-CH₂

CF₃ 6-F C0₂Et N-CH OCF3 7-Cl C0 Et N-CH₂

CF₃ 6-F i-Pr N-CH₂ OCF3 7-Cl i-Pr N-CH₂

CF₃ 6-F Me N-CH₂ OCF3 7-Cl Me N-CH₂

CF₃ 6-F 4-F-Ph N-CH₂ OCF3 7-Cl 4-F-Ph N-CH₂

CF₃ 7-F C0₂Me N-CH₂ OCF3 7-CF3 CO^e N- H₂

CF₃ 7-F C0₂Et N-CH₂ OCF3 7-CF3 C0₂Et N-CH₂

CF₃ 7-F i-Pr N-CH₂ OCF3 7-CF3 i-Pr N-CH₂

CF₃ 7-F Me N-CH₂ OCF₃ 7-CF3 Me N-CH₂

CF₃ 7-F 4-F-Ph N-CH₂ OCF₃ 7-CF3 4-F-Ph N-CH₂

^x B^ B

^J X B

¹ B

^<= B

^J X

Br 6-F C0 Me OCH₂Ph CF₃ 7-Cl C0₂Me OCH Ph

Br 6-F C0₂Et OCH₂Ph CF₃ 7-Cl C0₂Et OCH₂Ph

Br 6-F i-Pr OCH₂Ph CF₃ 7-Cl i-Pr OCH₂Ph

Br 6-F Me OCH₂Ph CF₃ 7-Cl Me OCH₂Ph

Br 6-F 4-F-Ph OCH₂Ph CF₃ 7-Cl 4-F-Ph OCH₂Ph

Br 7-F C0₂Me OCH₂Ph CF₃ 7-CF3 C0₂Me OCH Ph

Br 7-F C0₂Et OCH₂Ph CF₃ 7-CF3 C0₂Et OCH₂Ph

Br 7-F i-Pr OCH₂Ph CF₃ 7-CF3 i-Pr 0CH₂Ph

Br 7-F Me OCH₂Ph CF₃ 7-CF3 Me OCH Ph

Br 7-F 4-F-Ph OCH₂Ph CF₃ 7-CF3 4-F-Ph OCH₂Ph

Br 7-Cl C0₂Me OCH Ph OCF₃ 6-F C0₂Me OCH₂Ph

Br 7-Cl C0 Et OCH₂Ph OCF3 6-F C0₂Et OCH₂Ph

Br 7-Cl i-Pr OCH₂Ph OCF3 6-F i-Pr OCH₂Ph

Br 7-Cl Me OCH₂Ph OCF3 6-F Me OCH₂Ph

Br 7-Cl 4-F-Ph OCH₂Ph OCF3 6-F 4-F-Ph OCH₂Ph

Br 7-CF₃ C0₂Me OCH Ph OCF3 7-F C0₂Me OCH₂Ph

Br 7-CF₃ C0 Et OCH₂Ph OCF3 7-F C0₂Et OCH₂Ph

Br 7-CF₃ i-Pr OCH₂Ph OCF3 7-F i-Pr OCH₂Ph

Br 7~CF₃ Me OCH₂Ph OCF3 7-F Me OCH₂Ph

Br 7"CF₃ 4-F-Ph OCH₂Ph OCF3 7-F 4-F-Ph OCH₂Ph

CF₃ 6-F C0₂Me OCH₂Ph OCF3 7-Cl C0₂Me OCH₂Ph

CF₃ 6-F C0₂Et OCH₂Ph OCF3 7-Cl C0₂Et OCH Ph

CF₃ 6-F i-Pr OCH₂Ph OCF3 7-Cl i-Pr OCH₂Ph CF₃ 6-F Me OCH₂Ph OCF3 7-Cl Me OCH₂Ph CF₃ 6-F 4-F-Ph OCH₂Ph OCF3 7-Cl 4-F-Ph OCH₂Ph CF₃ 7-F C0₂Me OCH₂Ph OCF3 7-CF3 C0₂Me OCH₂Ph CF₃ 7-F C0₂Et OCH Ph OCF3 7-CF3 C0 Et OCH₂Ph CF₃ 7-F i-Pr OCH₂Ph OCF3 7-CF3 i-Pr OCH₂Ph CF₃ 7-F Me OCH₂Ph OCF3 7-CF3 Me OCH₂Ph CF₃ 7-F 4-F-Ph OCH₂Ph OCF3 7-CF3 4-F-Ph OCH₂Ph

¹ B^ B

^J X B

¹ B^ B

^J X

Br 6-F C0₂Me NHMe CF₃ 7-Cl C0 Me NHMe

Br 6-F C0₂Et NHMe C ₃ 7-Cl C0₂Et NHMe

Br 6-F i-Pr NHMe CF₃ 7-Cl i-Pr NHMe

Br 6-F Me NHMe CF₃ 7-Cl Me NHMe

Br 6-F 4-F-Ph NHMe CF₃ 7-Cl 4-F-Ph NHMe

Br 7-F C0₂Me NHMe CF₃ 7-CF₃ C0₂Me NHMe

Br 7-F C0₂Et NHMe CF₃ 7-CF₃ C0 Et NHMe

Br 7-F i-Pr NHMe CF₃ 7-CF₃ i-Pr NHMe

Br 7-F Me NHMe CF₃ 7-CF₃ Me NHMe

Br 7-F 4-F-Ph NHMe CF₃ 7-CF₃ 4-F-Ph NHMe

Br 7-Cl C0₂Me NHMe OCF₃ 6-F C0 Me NHMe

Br 7-Cl C0₂Et NHMe OCF₃ 6-F C0₂Et NHMe

Br 7-Cl i-Pr NHMe OCF₃ 6-F i-Pr NHMe

Br 7-Cl Me NHMe OCF₃ 6-F Me NHMe

Br 7-Cl 4-F-Ph NHMe OCF₃ 6-F 4-F-Ph NHMe

Br 7-CF₃ C0₂Me NHMe OCF₃ 7-F C0 Me NHMe

Br 7-CF₃ C0₂Et NHMe OCF₃ 7-F C0₂Et NHMe

Br 7-CF₃ i-Pr NHMe OCF₃ 7-F i-Pr NHMe

Br 7-CF₃ Me NHMe OCF₃ 7-F Me NHMe

Br 7-CF₃ 4-F-Ph NHMe OCF₃ 7-F 4-F-Ph NHMe

CF₃ 6-F C0₂Me NHMe OCF₃ 7-Cl C0₂Me NHMe

C ₃ 6-F C0₂Et NHMe OCF₃ 7-Cl C0₂Et NHMe CF₃ 6-F i-Pr NHMe OCF₃ 7-Cl i-Pr NHMe CF₃ 6-F Me NHMe OCF₃ 7-Cl Me NHMe CF₃ 6-F 4-F-Ph NHMe OCF₃ 7-Cl 4-F-Ph NHMe CF₃ 7-F C0 Me NHMe OCF₃ 7-CF₃ C0 Me NHMe CF₃ 7-F C0₂Et NHMe OCF₃ 7~CF₃ C0₂Et NHMe CF₃ 7-F i-Pr NHMe OCF₃ 7-CF₃ i-Pr NHMe CF₃ 7-F Me NHMe OCF₃ 7-CF₃ Me NHMe CF₃ 7-F 4-F-Ph NHMe OCF₃ 7-CF₃ 4-F-Ph NHMe

^A B

^<= B

^J X B

¹ B

^<= B

^J X

Br 6-F C0₂Me N-CH₂ CF3 7-Cl C0₂Me N-CH₂

Br 6-F C0 Et N-CH CF3 7-Cl C0₂Et N»CH₂

Br 6-F i-Pr N™CH₂ CF3 7-Cl i-Pr N-CH

Br 6-F Me N-CH₂ CF₃ 7-Cl Me N«-CH₂

Br 6-F 4-F-Ph CF3 7-Cl 4-F-Ph N-CH₂

Br 7-F C0₂Me N-CH₂ CF3 7-CF3 C0₂Me N-CH₂

Br 7-F C0₂Et N-CH₂ CF3 7-CF3 C0₂Et N-CH₂

Br 7-F i-Pr N-CH₂ CF₃ 7-CF3 i-Pr N-CH₂

Br 7-F Me N-CH₂ CF3 7-CF3 Me N-CH₂

Br 7-F 4-F-Ph N-CH₂ CF3 7-CF3 4-F-Ph N-CH₂

Br 7-Cl C0₂Me N-CH₂ OCF3 6-F C0₂Me N-CH₂

Br 7-Cl C0₂Et N-CH₂ OCF3 6-F C0 Et N-CH₂

Br 7-Cl i-Pr N-CH₂ OCF3 6-F i-Pr N-CH₂

Br 7-Cl Me N-CH₂ OCF3 6-F Me N-CH₂

Br 7-Cl 4-F-Ph N-CH₂ OCF3 6-F 4-F-Ph N-CH₂

Br 7-CF3 C0 Me N-CH₂ OCF3 7-F C0 Me N-CH₂

Br 7-CF3 C0₂Et N-CH₂ OCF3 7-F C0₂Et N-CH₂

Br 7-CF3 i-Pr N-CH₂ OCF3 7-F i-Pr N-CH₂

Br 7-CF3 Me N-CH₂ OCF3 7-F Me N-CH₂

Br 7-CF3 4-F-Ph N-CH₂ OCF3 7-F 4-F-Ph N-CH₂

CF₃ 6-F C0₂Me N-CH₂ OCF3 7-Cl C0₂Me N-CH₂

CF₃ 6-F C0₂Et N-CH₂ OCF3 7-Cl C0₂Et N-CH₂

CF₃ 6-F i-Pr N-CH₂ OCF3 7-Cl i-Pr N-CH₂

CF3 6-F Me N-CH₂ OCF3 7-Cl Me N-CH₂

CF3 6-F 4-F-Ph N-CH₂ OCF3 7-Cl 4-F-Ph N-CH₂

CF₃ 7-F C0₂Me N-CH₂ OCF3 7-CF3 C0₂Me N-CH₂

CF₃ 7-F C0₂Et N-CH₂ OCF3 7-CF3 C0 Et N-CH₂

CF3 7-F i-Pr N«CH OCF3 7-CF3 i-Pr N-CH₂

CF3 7-F Me N-CH₂ OCF3 7-CF3 Me N-CH₂

CF₃ 7-F 4-F-Ph N-CH₂ OCF3 7-CF3 4-F-Ph N-CH₂ B¹ B* B³ X B¹ B B³ X

Br 6-F CO^e N-CMe₂ CF₃ 7-Cl C0₂Me N-CMe₂

Br 6-F C0₂Et N-CMe₂ CF3 7-Cl C0₂Et N-CMe₂

Br 6-F i-Pr N-CMe₂ CF₃ 7-Cl i-Pr N-CMe

Br 6-F Me N-CMe₂ CF3 7-Cl Me N_CMe₂

Br 6-F 4-F-Ph N-CMe₂ CF3 7-Cl 4-F-Ph N-CMe₂

Br 7-F C0₂Me CF3 7-CF3 C0₂Me N-CMe₂

Br 7-F C0₂ ^Et CF3 7-CF3 C0₂Et N^βCM ₂

Br 7-F i-Pr CF3 7-CF3 i-Pr N"*CMe₂

Br 7-F Me N- fe₂ CF₃ 7-CF3 Me N-CMe₂

Br 7-F 4-F-Ph N-CMe CF₃ 7-CF3 4-F-Ph N-CMe₂

Br 7-Cl C0₂Me N-CMe OCF3 6-F C0₂Me N-CMe₂

Br 7-Cl C0₂Et N-CMe₂ OCF3 6-F C0 Et N-CMe₂

Br 7-Cl i-Pr N-CMe₂ i-Pr N-CMe₂

Br 7-Cl Me N-CMe₂ Me N-CMe₂

Br 7-Cl 4-F-Ph N-CMe₂ 4-F-Ph N-CMe₂

Br 7-CF3 CO^e N-CMe₂ CO^e N-CMe₂

Br 7-CF3 C0₂Et N-CMe₂ C0₂Et N-CMe₂

Br 7-CF3 i-Pr N-CMe₂ i-Pr N-CMe₂

Br 7-CF3 Me N-CMe₂

₂

Br 7-CF3 4-F-Ph N-CMe₂ OCF3 7-F 4-F-Ph N-CMe₂

CF₃ 6-F CO^e N-CMe₂ OCF3 7-Cl CO^e N-CMe₂

CF₃ 6-F C0₂Et N-CMe OCF3 7-Cl C0₂Et N-CMe₂

CF₃ 6-F i-Pr N-CMe₂ OCF3 7-Cl i-Pr N CMe₂

CF₃ 6-F Me N«CMe₂ OCF3 7-Cl Me N-CMe₂

CF₃ 6-F 4-F-Ph N-CMe₂ OCF3 7-Cl 4-F-Ph KM_Me₂

CF₃ 7-F C0₂Me OCF3 7-CF3 C0₂Me N-CMe₂

CF₃ 7-F C0₂Et OCF3 7-CF3 C0₂Et N-CMe₂

CF₃ 7-F i-Pr N-CMe₂ OCF3 7-CF3 i-Pr N-CMe₂

CF₃ 7-F Me N-CMe₂ OCF3 7-CF3 Me N-CMe₂

CF _, 7-F 4-F-Ph N-CMe₂ OCF3 7-CF3 4-F-Ph N-CMe₂ B¹ B B³ X B¹ B³ X

Br 6-F C0 Me N-CHPh CF₃ 7-Cl C0₂Me N-CHPh

Br 6-F C0₂Et N-CHPh CF₃ 7-Cl C0₂Et N-CHPh

Br 6-F i-Pr N-CHPh CF₃ 7-Cl i-Pr N-CHPh

Br 6-F Me N-CHPh CF₃ 7-Cl Me N-CHPh

Br 6-F 4-F-Ph N-CHPh CF₃ 7-Cl 4-F-Ph N-CHPh

Br 7-F C0₂Me N-CHPh CF₃ 7-CF3 C0₂Me N-CHPh

Br 7-F C0 Et N-CHPh CF₃ 7-CF3 C0₂Et N-CHPh

Br 7-F i-Pr N-CHPh CF₃ 7-CF3 i-Pr N-CHPh

Br 7-F Me N-CHPh CF₃ 7-CF3 Me N-CHPh

Br 7-F 4-F-Ph N-CHPh CF₃ 7-CF3 4-F-Ph f -CHPh

Br 7-Cl C0₂Me N-CHPh OCF₃ 6-F C0₂Me N-CHPh

Br 7-Cl C0₂Et N-CHPh OCF3 6-F C0₂Et N-CHPh

Br 7-Cl i-Pr N-CHPh OCF3 6-F i-Pr N-CHPh

Br 7-Cl Me N-CHPh OCF3 6-F Me N-CHPh

Br 7-Cl 4-F-Ph N-CHPh OCF3 6-F 4-F-Ph N-CHPh

Br 7-CF₃ C0₂Me N-CHPh OCF3 7-F C0₂Me N-CHPh

Br 7-CF₃ C0₂Et N-CHPh OCF3 7-F C0₂Et N-CHPh

Br 7-CF₃ i-Pr N-CHPh OCF3 7-F i-Pr N-CHPh

Br 7-CF₃ Me N-CHPh OCF3 7-F Me N-CHPh

Br 7-CF₃ 4-F-Ph N-CHPh OCF3 7-F 4-F-Ph N-CHPh

CF₃ 6-F C0₂Me N-CHPh OCF3 7-Cl C0₂Me N-CHPh

CF₃ 6-F C0₂Et N-CHPh OCF3 7-Cl C0₂Et N-CHPh

CF₃ 6-F i-Pr N-CHPh OCF3 7-Cl i-Pr N-CHPh

CF₃ 6-F Me N-CHPh OCF3 7-Cl Me N-CHPh

CF₃ 6-F 4-F-Ph N-CHPh OCF3 7-Cl 4-F-Ph N-CHPh

CF₃ 7-F C0₂Me N-CHPh OCF3 7-CF3 C0₂Me N-CHPh

CF₃ 7-F C0 Et N-CHPh OCF3 7-CF₃ C0 Et N-CHPh

CF₃ 7-F i-Pr N-CHPh OCF3 7-CF₃ i-Pr N-CHPh

CF₃ 7-F Me N-CHPh OCF3 7-CF₃ Me N-CHPh

CF₃ 7-F 4-F-Ph N-CHPh OCF3 7-CF₃ 4-F-Ph N-CHPh

^A B B

³ X

Br 6-F C0₂Me OMe

Br 6-F C0₂Et OMe

Br 6-F i-Pr OMe

Br 6-F Me OMe

Br 6-F 4-F-Ph OMe

Br 7-F CO^e OMe

Br 7-F C0₂Et OMe

Br 7-F i-Pr OMe

Br 7-F Me OMe

Br 7-F 4-F-Ph OMe

Br 7-Cl C0₂Me OMe

Br 7-Cl C0₂Et OMe

Br 7-Cl i-Pr OMe

Br 7-Cl Me OMe

Br 7-Cl 4-F-Ph OMe

Br 7-CF3 C0₂Me OMe

Br 7-CF3 C0₂Et OMe

Br 7-CF3 i-Pr OMe

Br 7-CF3 Me OMe

Br 7-CF3 4-F-Ph OMe

CF₃ 6-F C0₂Me OMe

CF₃ 6-F C0₂Et OMe

CF₃ 6-F i-Pr OMe

CF₃ 6-F Me OMe

CF₃ 6-F 4-F-Ph OMe

C ₃ 7-F C0₂Me OMe

CF₃ 7-F C0₂Et OMe

CF₃ 7-F i-Pr OMe

CF₃ 7-F Me OMe

CF₃ 7-F 4-F-Ph OMe

¹ X B

¹ B

^z B X

Br 6-F C0₂Me OCH₂Ph CF₃ 7-Cl C0₂Me OCH₂Ph

Br 6-F C0₂Et OCH Ph CF₃ 7-Cl C0₂Et OCH₂Ph

Br 6-F i-Pr OCH₂Ph CF₃ 7-Cl i-Pr OCH₂Ph

Br 6-F Me OCH₂Ph CF₃ 7-Cl Me OCH₂Ph

Br 6-F 4-F-Ph OCH₂Ph CF3 7-Cl 4-F-Ph OCH Ph

Br 7-F C0₂Me OCH₂Ph CF₃ 7-CF3 C0₂Me OCH₂Ph

Br 7-F C0₂Et OCH₂Ph CF₃ 7-CF3 C0 Et OCH₂Ph

Br 7-F i-Pr OCH₂Ph CF₃ 7-CF3 i-Pr OCH₂Ph

Br 7-F Me OCH Ph CF₃ 7-CF3 Me OCH₂Ph

Br 7-F 4-F-Ph OCH₂Ph CF₃ 7-CF3 4-F-Ph OCH₂Ph

Br 7-Cl C0₂Me OCH₂Ph OCF₃ 6-F C0 Me OCH Ph

Br 7-Cl C0 Et OCH₂Ph OCF3 6-F C0₂Et OCH₂Ph

Br 7-Cl i-Pr OCH₂Ph OCF3 6-F i-Pr OCH₂Ph

Br 7-Cl Me OCH₂Ph OCF3 6-F Me OCH₂Ph

Br 7-Cl 4-F-Ph OCH₂Ph OCF3 6-F 4-F-Ph OCH₂Ph

Br 7-CF₃ C0 Me OCH₂Ph OCF3 7-F C0₂Me OCH₂Ph

Br 7-CF₃ C0₂Et OCH₂Ph OCF3 7-F C0₂Et OCH₂Ph

Br 7-CF₃ i-Pr OCH₂Ph OCF3 7-F i-Pr OCH₂Ph

Br 7-CF₃ Me OCH₂Ph OCF3 7-F Me OCH₂Ph

Br 7-CF₃ 4-F-Ph OCH₂Ph OCF3 7-F 4-F-Ph OCH₂Ph

CF₃ 6-F C0₂Me OCH₂Ph OCF3 7-Cl C0₂Me OCH₂Ph

CF₃ 6-F C0₂Et OCH₂Ph OCF3 7-Cl C0₂Et OCH₂Ph

CF₃ 6-F i-Pr OCH₂Ph OCF3 7-Cl i-Pr OCH₂Ph

<= ₃ 6-F Me OCH₂Ph OCF3 7-Cl Me OCH Ph CF₃ 6-F 4-F-Ph OCH₂Ph OCF3 7-Cl 4-F-Ph OCH₂Ph CF₃ 7-F C0₂Me OCH Ph OCF3 7-CF3 C0₂Me OCH₂Ph CF₃ 7-F C0₂Et OCH₂Ph OCF3 7-CF3 C0 Et OCH₂Ph CF₃ 7-F i-Pr OCH₂Ph OCF3 7-CF3 i-Pr OCH₂Ph CF₃ 7-F Me OCH₂Ph OCF3 7-CF3 Me OCH₂Ph CF₃ 7-F 4-F-Ph OCH₂Ph OCF3 7-CF3 4-F-Ph OCH Ph

³ X

Br 6-F C0₂Me NHCHO

Br 6-F C0₂Et NHCHO

Br 6-F i-Pr NHCHO

Br 6-F Me NHCHO

Br 6-F 4-F-Ph NHCHO

Br 7-F CO^e NHCHO

Br 7-F C0₂Et NHCHO

Br 7-F i-Pr NHCHO

Br 7-F Me NHCHO

Br 7-F 4-F-Ph NHCHO

Br 7-Cl C0₂Me NHCHO

Br 7-Cl C0₂Et NHCHO

Br 7-Cl i-Pr NHCHO

Br 7-Cl Me NHCHO

Br 7-Cl 4-F-Ph NHCHO

Br 7-CF₃ C0 Me NHCHO

Br 7-CF₃ C0₂Et NHCHO

Br 7-CF₃ i-Pr NHCHO

Br 7-CF₃ Me NHCHO

Br 7-CF₃ 4-F-Ph NHCHO

CF₃ 6-F C0₂Me NHCHO

CF₃ 6-F C0₂Et NHCHO

CF₃ 6-F i-Pr NHCHO

CF₃ 6-F Me NHCHO

CF₃ 6-F 4-F-Ph NHCHO

CF₃ 7-F C0₂Me NHCHO

CF₃ 7-F C0 Et NHCHO

CF₃ 7-F i-Pr NHCHO

C ₃ 7-F Me NHCHO CF₃ 7-F 4-F-Ph NHCHO

¹ B

^<= B

^J X B

¹ B^ B X

Br 6-F C0₂Me NH(CO)Me CF₃ 7-Cl C0₂Me NH(CO)Me

Br 6-F C0₂Et NH(CO)Me CF₃ 7-Cl C0₂Et NH(CO)Me

Br 6-F i-Pr NH(CO)Me CF₃ 7-Cl i-Pr NH(CO)Me

Br 6-F Me NH(CO)Me CF₃ 7-Cl Me NH(CO)Me

Br 6-F 4-F-Ph NH(CO)Me CF₃ 7-Cl 4-F-Ph NH(CO)Me

Br 7-F C0₂Me NH(CO)Me CF₃ 7-CF3 C0₂Me NH(CO)Me

Br 7-F C0₂Et NH(CO)Me CF₃ 7-CF3 C0₂Et NH(CO)Me

Br 7-F i-Pr NH(CO)Me CF₃ 7-CF3 i-Pr NH(CO)Me

Br 7-F Me NH(CO)Me CF₃ 7-CF3 Me NH(CO)Me

Br 7-F 4-F-Ph NH(CO)Me CF₃ 7-CF3 4-F-Ph NH(CO)Me

Br 7-Cl C0₂Me NH(CO)Me OCF₃ 6-F C0₂Me NH(CO)Me

Br 7-Cl C0₂Et NH(CO)Me OCF3 6-F C0₂Et NH(CO)Me

Br 7-Cl i-Pr NH(CO)Me OCF3 6-F i-Pr NH(CO)Me

Br 7-Cl Me NH(CO)Me OCF3 6-F Me NH(CO)Me

Br 7-Cl 4-F-Ph NH(CO)Me OCF3 6-F 4-F-Ph NH(CO)Me

Br 7-CF₃ C0₂Me NH(CO)Me OCF3 7-F C0₂Me NH(CO)Me

Br 7-CF₃ C0₂Et NH(CO)Me OCF3 7-F C0₂Et NH(CO)Me

Br 7-CF₃ i-Pr NH(CO)Me OCF3 7-F i-Pr NH(CO)Me

Br 7-CF₃ Me NH(CO)Me OCF3 7-F Me NH(CO)Me

Br 7~CF₃ 4-F-Ph NH(CO)Me OCF3 7-F 4-F-Ph NH(CO)Me

CF₃ 6-F C0₂Me NH(CO)Me OCF3 7-Cl C0 Me NH(CO)Me

CF₃ 6-F C0₂Et NH(CO)Me OCF3 7-Cl C0₂Et NH(CO)Me

CF₃ 6-F i-Pr NH(CO)Me OCF3 7-Cl i-Pr NH(CO)Me

CF₃ 6-F Me NH(CO)Me OCF3 7-Cl Me NH(CO)Me

CF₃ 6-F 4-F-Ph NH(CO)Me OCF3 7-Cl 4-F-Ph NH(CO)Me

CF₃ 7-F C0₂Me NH(CO)Me OCF3 7-CF3 C0₂Me NH(CO)Me

CF₃ 7-F C0₂Et NH(CO)Me OCF3 7-CF3 C0₂Et NH.CO.Me

CF₃ 7-F i-Pr NH(CO)Me OCF3 7-CF3 i-Pr NH(CO)Me

CF₃ 7-F Me NH(CO)Me OCF3 7-CF3 Me NH(CO)Me

CF₃ 7-F 4-F-Ph NH(CO)Me OCF3 7-CF3 4-F-Ph NH(CO)Me

^x B* B

^J X B

¹ B B

^J X

Br 6-F C0 Me N-CMe₂ CF₃ 7-Cl C0₂Me N-CMe₂

Br 6-F C0 Et N-CMe₂ CF3 7-Cl C0₂Et N-CMe₂

Br 6-F i-Pr _*_CMe₂ CF3 7-Cl i-Pr N-CMe₂

Br 6-F Me w^—CMe₂ CF3 7-Cl Me N-α e₂

Br 6-F 4-F-Ph N-CMe CF₃ 7-Cl 4-F-Ph N-CMe₂

Br 7-F CO2M& N-CMe₂ CF3 7-CF3 C0₂Me N-CMe₂

Br 7-F C0₂Et N-CMe₂ CF3 7-CF3 C0₂Et

Br 7-F i-Pr N-CMe₂ CF₃ 7-CF3 i-Pr N-CMe₂

Br 7-F Me N-CMe₂ CF3 7-CF3 Me N-CMe₂

Br 7-F 4-F-Ph N _Me₂ CF3 7-CF3 4-F-Ph N-CMe₂

Br 7-Cl C0₂Me N-CMe₂ OCF3 6-F C0₂Me N _Me

Br 7-Cl C0₂Et N-CMe₂ OCF3 6-F C0₂Et N-CMe

Br 7-Cl i-Pr N-CMe₂ OCF3 6-F i-Pr N-CMe₂

Br 7-Cl Me N- _e₂ OCF3 6-F Me N-CMe

Br 7-Cl 4-F-Ph N«CMe₂ OCF3 6-F 4-F-Ph N-CMe₂

Br 7-CF₃ C0₂Me N-CMe₂ OCF3 7-F C0₂Me N-CMe₂

Br 7-CF₃ C0 Et N-CMe OCF3 7-F C0₂Et N-CMe₂

Br 7-CF₃ i-Pr N-CMe OCF3 7-F i-Pr N-CMe₂

Br 7-CF₃ Me N-CMe₂ OCF3 7-F Me N-CMe₂

Br 7-CF₃ 4-F-Ph N-CMe OCF3 7-F 4-F-Ph N-CMe₂

CF₃ 6-F C0₂Me N>"CMe₂ OCF3 7-Cl C0₂Me N-CMe₂

C ₃ 6-F C0₂Et N-CMe₂ OCF3 7-Cl C0₂Et N-CMe₂

CF₃ 6-F i-Pr N«CMe₂ OCF3 7-Cl i-Pr N«»CMe₂

CF₃ 6-F Me N-CMe₂ OCF3 7-Cl Me N-CMe₂

CF₃ 6-F 4-F-Ph N-CMe₂ OCF3 7-Cl 4-F-Ph NK_Me₂

CF₃ 7-F C0₂Me N-CMe₂ OCF3 7-CF3 CO^e !W_Me₂

CF₃ 7-F C0₂Et N-CMe₂ OCF3 7-CF3 C0₂Et N 3_e₂

CF₃ 7-F i-Pr N-CMe₂ OCF₃ 7-CF3 i-Pr »M31e₂

CF₃ 7-F Me N-CMe₂ OCF₃ 7-CF3 Me N-CMe₂

CF₃ 7-F 4-F-Ph N_CMe₂ OCF₃ 7-CF3 4-F-Ph N-CMe₂ B¹ B* B^J X ^x B* B³ X

Br 6-F C0 Me N-CHPh CF₃ 7-Cl C0₂Me N-CHPh

Br 6-F C0₂Et N-CHPh CF₃ 7-Cl C0₂Et N-CHPh

Br 6-F i-Pr N-CHPh CF3 7-Cl i-Pr N-CHPh

Br 6-F Me N-CHPh CF3 7-Cl Me N-CHPh

Br 6-F 4-F-Ph N-CHPh CF₃ 7-Cl 4-F-Ph N-CHPh

Br 7-F C0₂Me N-CHPh CF₃ 7-CF3 C0₂Me N-CHPh

Br 7-F C0₂Et N-CHPh CF₃ 7-CF3 C0₂Et N-CHPh

Br 7-F i-Pr N-CHPh CF3 7-CF3 i-Pr N-CHPh

Br 7-F Me N-CHPh CF3 7-CF3 Me N-CHPh

Br 7-F 4-F-Ph N-CHPh CF3 7-CF3 4-F-Ph N-CHPh

Br 7-Cl C0₂Me N-CHPh OCF3 6-F C0₂Me N-CHPh

Br 7-Cl C0₂Et N-CHPh OCF3 6-F C0₂Et N-CHPh

Br 7-Cl i-Pr N-CHPh OCF3 6-F i-Pr N-CHPh

Br 7-Cl Me N-CHPh OCF3 6-F Me N-CHPh

Br 7-Cl 4-F-Ph N-CHPh OCF3 6-F 4-F-Ph N-CHPh

Br 7-CF3 C0₂Me N-CHPh OCF3 7-F C0 Me N-CHPh

Br 7-CF3 C0₂Et N-CHPh OCF3 7-F C0₂Et N-CHPh

Br 7-CF3 i-Pr N-CHPh OCF3 7-F i-Pr N-CHPh

Br 7-CF3 Me N-CHPh OCF3 7-F Me N-CHPh

Br 7-CF3 4-F-Ph N-CHPh OCF3 7-F 4-F-Ph N-CHPh

CF₃ 6-F C0₂Me N-CHPh OCF3 7-Cl C0₂Me N-CHPh

CF₃ 6-F C0 Et N-CHPh OCF3 7-Cl C0₂Et N-CHPh

CF₃ 6-F i-Pr N-CHPh OCF3 7-Cl i-Pr N-CHPh

CF₃ 6-F Me N-CHPh OCF3 7-Cl Me N-CHPh

CF₃ 6-F 4-F-Ph N-CHPh OCF3 7-Cl 4-F-Ph N-CHPh CF₃ 7-F C0₂Me N-CHPh OCF3 7-CF3 C0₂Me N-CHPh

CF₃ 7-F C0₂Et N-CHPh OCF3 7-CF3 C0₂Et N-CHPh

CF₃ 7-F i-Pr N-CHPh OCF3 7-CF3 i-Pr N-CHPh

CF₃ 7-F Me N-CHPh OCF3 7-CF3 Me N-CHPh

CF₃ 7-F 4-F-Ph N-CHPh OCF3 7-CF3 4-F-Ph N-CHPh

^x B

^z B

³ X B

¹ B

^<= B

³ X

Br 6-F CO^e OMe CF₃ 7-Cl C0 Me OMe

Br 6-F C0₂Et OMe CF₃ 7-Cl C0₂Et OMe

Br 6-F i-Pr OMe CF₃ 7-Cl i-Pr OMe

Br 6-F Me OMe CF₃ 7-Cl Me OMe

Br 6-F 4-F-Ph OMe CF₃ 7-Cl 4-F-Ph OMe

Br 7-F CO^e OMe CF₃ 7-CF3 C0₂Me OMe

Br 7-F C0₂Et OMe CF₃ 7-CF3 C0₂Et OMe

Br 7-F i-Pr OMe CF₃ 7-CF3 i-Pr OMe

Br 7-F Me OMe CF₃ 7-CF3 Me OMe

Br 7-F 4-F-Ph OMe CF₃ 7-CF3 4-F-Ph { OMe

Br 7-Cl Cθ₂Me OMe OCF3 6-F Cθ₂Me OMe

Br 7-Cl C0₂Et OMe OCF3 6-F C0₂Et OMe

Br 7-Cl i-Pr OMe OCF3 6-F i-Pr OMe

Br 7-Cl Me OMe OCF3 6-F Me OMe

Br 7-Cl 4-F-Ph OMe OCF3 6-F 4-F-Ph OMe

Br 7-CF3 C0 Me OMe OCF3 7-F C0₂Me OMe

Br 7-CF3 C0 Et OMe OCF3 7-F C0₂Et OMe

Br 7-CF3 i-Pr OMe OCF3 7-F i-Pr OMe

Br 7-CF3 Me OMe OCF3 7-F Me OMe

Br 7-CF3 4-F-Ph OMe OCF3 7-F 4-F-Ph OMe

CF₃ 6-F C0₂Me OMe OCF3 7-Cl C0₂Me OMe CF₃ 6-F C0₂Et OMe OCF3 7-Cl C0₂Et OMe CF₃ 6-F i-Pr OMe OCF3 7-Cl i-Pr OMe CF₃ 6-F Me OMe OCF3 7-Cl Me OMe CF₃ 6-F 4-F-Ph OMe OCF3 7-Cl 4-F-Ph OMe

CF₃ 7-F C0₂Me OMe OCF3 7-CF3 C0₂Me OMe CF₃ 7-F C0₂Et OMe OCF3 7-CF3 C0 Et OMe CF₃ 7-F i-Pr OMe OCF3 7-CF3 i-Pr OMe CF₃ 7-F Me OMe OCF3 7-CF3 Me OMe CF₃ 7-F 4-F-Ph OMe OCF3 7-CF3 4-F-Ph OMe B^A B^J X B¹ B^Z B^J X

Br 6-F C0₂Me OCH₂Ph CF₃ 7-Cl C0₂Me OCH₂Ph

Br 6-F C0₂Et OCH₂Ph CF₃ 7-Cl C0₂Et OCH₂Ph

Br 6-F . i-Pr OCH₂Ph CF₃ 7-Cl i-Pr OCH₂Ph

Br 6-F Me OCH₂Ph CF₃ 7-Cl Me OCH Ph

Br 6-F 4-F-Ph OCH₂Ph CF₃ 7-Cl 4-F-Ph OCH₂Ph

Br 7-F C0₂Me OCH₂Ph CF₃ 7-CF₃ C0₂Me OCH₂Ph

Br 7-F C0₂Et OCH₂Ph CF₃ 7-CF₃ C0₂Et OCH Ph

Br 7-F i-Pr OCH₂Ph CF₃ 7-CF₃ i-Pr OCH₂Ph

Br 7-F Me OCH₂Ph CF₃ 7-CF₃ Me OCH Ph

Br 7-F 4-F-Ph OCH₂Ph CF₃ 7-CF₃ 4-F-Ph OCH₂Ph

Br 7-Cl C0₂Me OCH₂Ph OCF₃ 6-F C0₂Me OCH₂Ph

Br 7-Cl C0₂Et OCH₂Ph OCF₃ 6-F C0₂Et OCH₂Ph

Br 7-Cl i-Pr OCH₂Ph OCF₃ 6-F i-Pr OCH Ph

Br 7-Cl Me OCH₂Ph CF₃ 6-F Me OCH₂Ph

Br 7-Cl 4-F-Ph OCH₂Ph OCF₃ 6-F 4-F-Ph OCH₂Ph

Br 7-CF₃ C0₂Me OCH₂Ph OCF₃ 7-F C0₂Me OCH₂Ph

Br 7-CF₃ C0₂Et OCH₂Ph OCF₃ 7-F C0₂Et OCH₂Ph

Br 7-CF₃ i-Pr OCH₂Ph OCF₃ 7-F i-Pr OCH₂Ph

Br 7-CF₃ Me OCH₂Ph OCF₃ 7-F Me OCH₂Ph

Br 7-CF₃ 4-F-Ph OCH Ph OCF₃ 7-F 4-F-Ph OCH₂Ph

CF₃ 6-F C0₂Me OCH₂Ph OCF₃ 7-Cl C0₂Me OCH₂Ph

C ₃ 6-F C0₂Et OCH₂Ph OCF₃ 7-Cl C0₂Et OCH₂Ph CF₃ 6-F i-Pr OCH₂Ph OCF₃ 7-Cl i-Pr OCH₂Ph CF₃ 6-F Me OCH₂Ph OCF₃ 7-Cl Me OCH₂Ph CF₃ 6-F 4-F-Ph OCH₂Ph OCF₃ 7-Cl 4-F-Ph OCH₂Ph CF₃ 7-F C0₂Me OCH₂Ph OCF₃ 7-CF₃ C0₂Me OCH₂Ph CF₃ 7-F C0₂Et OCH₂Ph OCF₃ 7-CF₃ C0₂Et OCH₂Ph CF₃ 7-F i-Pr OCH Ph OCF₃ 7-CF₃ i-Pr OCH₂Ph CF₃ 7-F Me OCH₂Ph OCF₃ 7~CF₃ Me OCH₂Ph CF₃ 7-F 4-F-Ph OCH₂Ph OCF₃ 7-CF₃ 4-F-Ph OCH₂Ph

¹ B B

^J X B

¹ B^ B

^J X

Br 6-F C0₂Me NHMe CF₃ 7-Cl C0₂Me NHMe

Br 6-F C0₂Et NHMe CF₃ 7-Cl C0 Et NHMe

Br 6-F i-Pr NHMe CF₃ 7-Cl i-Pr NHMe

Br 6-F Me NHMe CF₃ 7-Cl Me NHMe

Br 6-F 4-F-Ph NHMe CF₃ 7-Cl 4-F-Ph NHMe

Br 7-F C0₂Me NHMe C ₃ 7-CF3 C0₂Me NHMe

Br 7-F C0₂Et NHMe CF₃ 7-CF3 C0₂Et NHMe

Br 7-F i-Pr NHMe CF₃ 7-CF3 i-Pr NHMe

Br 7-F Me NHMe CF3 7-CF3 Me NHMe

Br 7-F 4-F-Ph NHMe CF3 7-CF3 4-F-Ph NHMe

Br 7-Cl C0₂Me NHMe OCF3 6-F C0₂Me NHMe

Br 7-Cl C0₂Et NHMe OCF3 6-F C0 Et NHMe

Br 7-Cl i-Pr NHMe OCF3 6-F i-Pr NHMe

Br 7-Cl Me NHMe OCF3 6-F Me NHMe

Br 7-Cl 4-F-Ph NHMe OCF3 6-F 4-F-Ph NHMe

Br 7-CF₃ C0₂Me NHMe OCF3 7-F C0₂Me NHMe

Br 7-CF₃ C0₂Et NHMe OCF3 7-F C0₂Et NHMe

Br 7-CF₃ i-Pr NHMe OCF3 7-F i-Pr NHMe

Br 7-CF₃ Me NHMe OCF3 7-F Me NHMe

Br 7-CF₃ 4-F-Ph NHMe OCF3 7-F 4-F-Ph NHMe

CF₃ 6-F C0₂Me NHMe OCF3 7-Cl C0₂Me NHMe

CF₃ 6-F C0₂Et NHMe OCF3 7-Cl C0 Et NHMe

CF₃ 6-F i-Pr NHMe OCF3 7-Cl i-Pr NHMe

CF₃ 6-F Me NHMe OCF3 7-Cl Me NHMe

CF₃ 6-F 4-F-Ph NHMe OCF3 7-Cl 4-F-Ph NHMe

CF₃ 7-F C0₂Me NHMe OCF3 7-CF3 C0₂Me NHMe CF₃ 7-F C0₂Et NHMe OCF3 7-CF3 C0₂Et NHMe CF₃ 7-F i-Pr NHMe OCF3 7-CF3 i-Pr NHMe CF₃ 7-F Me NHMe OCF3 7-CF3 Me NHMe CF₃ 7-F 4-F-Ph NHMe OCF3 7-CF3 4-F-Ph NHMe

^<= B

³ X B

¹ B

^<= B

^J X

Br 6-F C0₂Me NH.CO.Me CF₃ 7-Cl C0₂Me NH(CO)Me

Br 6-F C0₂Et NH(CO)Me CF3 7-Cl C0₂Et NH(CO)Me

Br 6-F i-Pr NH(CO)Me CF₃ 7-Cl i-Pr NH(CO)Me

Br 6-F Me NH(CO)Me CF₃ 7-Cl Me NH(CO)Me

Br 6-F 4-F-Ph NH(CO)Me CF3 7-Cl 4-F-Ph NH(CO)Me

Br 7-F C0 Me NH(CO)Me CF3 7-CF3 CO^e NH(CO)Me

Br 7-F C0₂Et NH(CO)Me CF3 7-CF3 C0₂Et NH(CO)Me

Br 7-F i-Pr NH(CO)Me CF3 7-CF3 i-Pr NH(CO)Me

Br 7-F Me NH(CO)Me CF₃ 7-CF3 Me NH(CO)Me

Br 7-F 4-F-Ph NH(CO)Me CF3 7-CF3 4-F-Ph NH(CO)Me

Br 7-Cl C0₂Me NH(CO)Me OCF3 6-F C0₂Me NH(CO)Me

Br 7-Cl C0₂Et NH(CO)Me OCF3 6-F C0₂Et NH(CO)Me

Br 7-Cl i-Pr NH(CO)Me OCF3 6-F i-Pr NH(CO)Me

Br 7-Cl Me NH(CO)Me OCF3 6-F Me NH(CO)Me

Br 7-Cl 4-F-Ph NH(CO)Me OCF3 6-F 4-F-Ph NH(CO)Me

Br 7-CF3 C0₂Me NH(CO)Me OCF3 7-F C0₂Me NH(CO)Me

Br 7-CF3 C0₂Et NH(CO)Me OCF3 7-F C0₂Et NH(CO)Me

Br 7-CF3 i-Pr NH(CO)Me OCF3 7-F i-Pr NH(CO)Me

Br 7-CF3 Me NH(CO)Me OCF3 7-F Me NH(CO)Me

Br 7-CF3 4-F-Ph NH(CO)Me OCF3 7-F 4-F-Ph NH(CO)Me

CF₃ 6-F C0₂Me NH(CO)Me OCF3 7-Cl C0₂Me NH(CO)Me

CF₃ 6-F C0₂Et NH(CO)Me OCF3 7-Cl C0₂Et NH(CO)Me

CF₃ 6-F i-Pr NH(CO)Me OCF3 7-Cl i-Pr NH(CO)Me

CF₃ 6-F Me NH(CO)Me OCF3 7-Cl Me NH(CO)Me

CF₃ 6-F 4-F-Ph NH(CO)Me OCF3 7-Cl 4-F-Ph NH(CO)Me

CF₃ 7-F C0₂Me NH(CO)Me OCF3 7-CF3 C0 Me NH(CO)Me

CF₃ 7-F C0 Et NH(CO)Me OCF3 7-CF3 C0₂Et NH(CO)Me

CF₃ 7-F i-Pr NH(CO)Me OCF3 7-CF3 i-Pr NH(CO)Me

CF₃ 7-F Me NH(CO)Me OCF3 7-CF3 Me NH(CO)Me

CF₃ 7-F 4-F-Ph NH(CO)Me OCF3 7-CF3 4-F-Ph NH(CO)Me

^x B B

^J X B

¹ B

^J -X

Br 6-F C0 Me N-CH₂ CF₃ 7-Cl C0₂Me N-CH₂

Br 6-F C0₂Et N-CH₂ CF₃ 7-Cl C0₂Et N-CH₂

Br 6-F i-Pr CF3 7-Cl i-Pr N-CH₂

Br 6-F Me N™CH9 CF₃ 7-Cl Me N-CH₂

Br 6-F 4-F-Ph N-CH₂ CF3 7-Cl 4-F-Ph N-CH₂

Br 7-F C0₂Me N-CH₂ CF3 7-CF3 C0 Me "CH₂

Br 7-F C0₂Et N-CH₂ CF₃ 7-CF3 C0₂Et N—CH₂

Br 7-F i-Pr N-CH₂ CF₃ 7-CF3 i-Pr N-CH₂

Br 7-F Me N :H₂ CF₃ 7-CF3 Me N-CH

Br 7-F 4-F-Ph N-CH CF₃ 7-CF3 4-F-Ph N«CH

Br 7-Cl C0 Me N-CH₂ OCF₃ 6-F C0₂Me N-CH₂

Br 7-Cl C0₂Et N-CH₂ OCF3 6-F C0 Et N-CH₂

Br 7-Cl i-Pr N-CH₂ OCF3 6-F i-Pr N-CH₂

Br 7-Cl Me N-CH₂ OCF3 6-F Me N-CH₂

Br 7-Cl 4-F-Ph N-CH₂ OCF3 6-F 4-F-Ph N-CH₂

Br 7"CF₃ C0Me N-CH₂ OCF3 7-F C0₂Me N-CH₂

Br 7-CF₃ C0₂Et N-CH₂ OCF3 7-F C0₂Et N-CH₂

Br 7-CF₃ i-Pr N-CH₂ OCF3 7-F i-Pr N-CH₂

Br 7"CF₃ Me N-CH₂ OCF3 7-F Me N-CH₂

Br 7"CF₃ 4-F-Ph N-CH OCF3 7-F 4-F-Ph N-CH₂

CF3 6-F C0₂Me N"CH₂ OCF3 7-Cl C0₂Me N-CH₂

CF₃ 6-F C0₂Et N-CH₂ OCF3 7-Cl C0 Et N-CH₂

CF₃ 6-F i-Pr N-CH₂ OCF3 7-Cl i-Pr N-CH₂

CF₃ 6-F Me N-CH₂ OCF3 7-Cl Me N-CH₂

CF₃ 6-F 4-F-Ph N-CH₂ OCF3 7-Cl 4-F-Ph N-CH₂

CF₃ 7-F C0₂Me N-CH₂ OCF3 7-CF3 C0₂Me N-CH₂

CF₃ 7-F C0₂Et N-CH₂ OCF3 7-CF3 C0₂Et N-CH₂

CF₃ 7-F i-Pr N-CH OCF3 7-CF3 i-Pr N-CH₂

CF₃ 7-F Me N-CH₂ OCF3 7-CF3 Me N-CH₂

CF₃ 7-F 4-F-Ph N-CH₂ OCF3 7-CF3 4-F-Ph N-CH

¹ B

^J X

Br 6-F C0₂Me N-CHPh

Br 6-F C0₂Et N-CHPh

Br 6-F i-Pr N-CHPh

Br 6-F Me N-CHPh

Br 6-F 4-F-Ph N-CHPh

Br 7-F C0 Me N-CHPh

Br 7-F C0₂Et N-CHPh

Br 7-F i-Pr N-CHPh

Br 7-F Me N-CHPh

Br 7-F 4-F-Ph N-CHPh

Br 7-Cl C0₂Me N-CHPh

Br 7-Cl C0₂Et N-CHPh

Br 7-Cl i-Pr N-CHPh

Br 7-Cl Me N-CHPh

Br 7-Cl 4-F-Ph N-CHPh

Br 7-CF₃ C0₂Me N-CHPh

Br 7-CF₃ C0₂Et N-CHPh

Br 7-CF₃ i-Pr N-CHPh

Br 7-CF₃ Me N-CHPh

Br 7-CF₃ 4-F-Ph N-CHPh

CF₃ 6-F C0₂Me N-CHPh

CF₃ 6-F C0 Et N-CHPh CF₃ 6-F i-Pr N-CHPh CF₃ 6-F Me N-CHPh CF₃ 6-F 4-F-Ph N-CHPh CF₃ 7-F C0₂Me N-CHPh CF₃ 7-F C0₂Et N-CHPh CF₃ 7-F i-Pr N-CHPh CF₃ 7-F Me N-CHPh CF₃ 7-F 4-F-Ph N-CHPh

³ X

Br 6-F C0₂Me OMe

Br 6-F C0₂Et OMe

Br 6-F i-Pr OMe

Br 6-F Me OMe

Br 6-F 4-F-Ph OMe

Br 7-F C0₂Me OMe

Br 7-F C0₂Et OMe

Br 7-F i-Pr OMe

Br 7-F Me OMe

Br 7-F 4-F-Ph OMe

Br 7-Cl C0₂Me OMe

Br 7-Cl C0₂Et OMe

Br 7-Cl i-Pr OMe

Br 7-Cl Me OMe

Br 7-Cl 4-F-Ph OMe

Br 7-CF₃ C0₂Me OMe

Br 7-CF₃ C0₂Et OMe

Br 7-CF₃ i-Pr OMe

Br 7~CF₃ Me OMe

Br 7-CF₃ 4-F-Ph OMe

CF₃ 6-F C0₂Me OMe

CF₃ 6-F C0₂Et OMe

C ₃ 6-F i-Pr OMe

CF₃ 6-F Me OMe

CF₃ 6-F 4-F-Ph OMe

CF₃ 7-F CO^e OMe

CF₃ 7-F C0₂Et OMe

CF₃ 7-F i-Pr OMe

C ₃ 7-F Me OMe

CF, 7-F 4-F-Ph OMe

¹ B^

^J X B

^x B

³ X

Br 6-F C0₂Me OCH₂Ph CF₃ 7-Cl C0₂Me OCH₂Ph

Br 6-F C0₂Et OCH₂Ph CF₃ 7-Cl C0₂Et OCH₂Ph

Br 6-F i-Pr OCH₂Ph CF₃ 7-Cl i-Pr OCH₂Ph

Br 6-F Me OCH₂Ph CF₃ 7-Cl Me OCH₂Ph

Br 6-F 4-F-Ph OCH₂Ph CF₃ 7-Cl 4-F-Ph OCH₂Ph

Br 7-F C0₂Me OCH₂Ph CF₃ 7-CF3 C0 Me OCH₂Ph

Br 7-F C0 Et OCH₂Ph CF₃ 7-CF3 C0₂Et OCH₂Ph

Br 7-F i-Pr OCH₂Ph CF₃ 7-CF3 i-Pr OCH₂Ph

Br 7-F Me OCH₂Ph CF₃ 7-CF3 Me OCH₂Ph

Br 7-F 4-F-Ph OCH₂Ph CF₃ 7-CF3 4-F-Ph I)CH₂Ph

Br 7-Cl C0₂Me OCH₂Ph OCF₃ 6-F C0₂Me OCH₂Ph

Br 7-Cl C0₂Et OCH₂Ph OCF₃ 6-F C0₂Et OCH₂Ph

Br 7-Cl i-Pr OCH₂Ph OCF₃ 6-F i-Pr OCH₂Ph

Br 7-Cl Me OCH₂Ph OCF₃ 6-F Me OCH₂Ph

Br 7-Cl 4-F-Ph OCH₂Ph OCF₃ 6-F 4-F-Ph OCH₂Ph

Br 7-CF₃ C0₂Me OCH₂Ph OCF₃ 7-F C0₂Me OCH₂Ph

Br 7-CF₃ C0₂Et OCH₂Ph OCF₃ 7-F C0₂Et OCH₂Ph

Br 7-CF₃ i-Pr OCH₂Ph OCF₃ 7-F i-Pr OCH₂Ph

Br 7-CF₃ Me OCH₂Ph OCF₃ 7-F Me OCH₂Ph

Br 7-CF₃ 4-F-Ph OCH₂Ph OCF₃ 7-F 4-F-Ph OCH₂Ph

CF₃ 6-F C0 Me OCH₂Ph OCF₃ 7-Cl C0 Me OCH₂Ph

CF₃ 6-F C0₂Et OCH₂Ph OCF₃ 7-Cl C0₂Et OCH₂Ph

C ₃ 6-F i-Pr OCH₂Ph OCF₃ 7-Cl i-Pr OCH₂Ph CF₃ 6-F Me OCH₂Ph OCF₃ 7-Cl Me OCH Ph CF₃ 6-F 4-F-Ph OCH₂Ph OCF3 7-Cl 4-F-Ph OCH₂Ph CF₃ 7-F C0₂Me OCH₂Ph OCF3 7-CF3 C0₂Me OCH₂Ph CF₃ 7-F C0₂Et OCH₂Ph OCF3 7-CF3 C0₂Et OCH₂Ph CF₃ 7-F i-Pr OCH₂Ph OCF3 7-CF3 i-Pr OCH₂Ph C ₃ 7-F Me OCH₂Ph OCF3 7-CF3 Me OCH₂Ph C ₃ 7-F 4-F-Ph OCH₂Ph OCF3 7-CF3 4-F-Ph OCH₂Ph

B¹ B* B^J X B¹ B B³ X Br 7-F 4-F-Ph NHC0₂Me Br 7-F 4-F-Ph NHS0₂NHMe

CF₃ 7-F 4-F-Ph NHCO^e CF₃ 7-F 4-F-Ph NHS0₂NHMe

OCF3 7-F 4-F-Ph NHC0₂Me OCF3 7-F 4-F-Ph NHS0₂NHMe

CF3 7-Cl C0₂Me HCO^e CF3 7-Cl CO_jgMe NHS0₂NHMe

OCF3 7-Cl CO^e NHC0₂Me OCF3 7-Cl C0 Me NHS0₂NHMe

OCF3 7-Cl C0₂Et NHC0 Me OCF3 7-Cl C0₂Et NHS0₂NHMe

Br 7-F 4-F-Ph NHC0₂Et Br 7-F 4-F-Ph NH(4-F-Ph) CF₃ 7-F 4-F-Ph NHC0₂Et CF₃ 7-F 4-F-Ph NH(4-F-Ph)

OCF3 7-F 4-F-Ph NHC0₂Et OCF3 7-F 4-F-Ph NH(4-F-Ph)

CF3 7-Cl C0₂Me NHC0₂Et CF₃ 7-Cl CO^e NH(4-F-Ph)

OCF3 7-Cl C0₂Me NHC0₂Et OCF3 7-Cl C0₂Me NH(4-F-Ph)

OCF3 7-Cl C0 Et NHC0₂Et OCF3 7-Cl C0₂Et NH(4-F-Ph)

Br 7-F 4-F-Ph NHS0 NH₂ Br 7-F 4-F-Ph NH(4-MeO-Ph)

CF₃ 7-F 4-F-Ph NHS0₂NH₂ CF₃ 7-F 4-F-Ph NH(4-MeO-Ph) OCF3 7-F 4-F-Ph NHS0 NH₂ OCF3 7-F 4-F-Ph NH(4-MeO-Ph)

CF₃ 7-Cl C0₂Me NHS0₂NH₂ CF3 7-Cl C0₂Me NH(4-MeO-Ph)

OCF3 7-Cl C0₂Me NHS0₂NH₂ OCF3 7-Cl C0₂Me NH(4-MeO-Ph) OCF3 7-Cl C0₂Et NHS0₂NH₂ OCF3 7-Cl C0₂Et NH(4-MeO-Ph)

Br 7-F 4-F-Ph NHS0 NHPh Br 7-F 4-F-Ph NHCH₂C_CH

CF₃ 7-F 4-F-Ph NHS0₂NHPh CF3 7-F 4-F-Ph NHCH₂C-CH

OCF3 7-F 4-F-Ph NHS0₂NHPh OCF3 7-F 4-F-Ph NHCH₂C_CH

CF3 7-Cl C0₂Me NHS0₂NHPh CF₃ 7-Cl C0₂Me NHCH₂C_CH

OCF3 7-Cl C0₂Me NHS0₂NHPh OCF3 7-Cl C0₂Me NHCH₂C_CH

OCF3 7-Cl C0₂Et NHS0 NHPh OCF3 7-Cl C0 Et NHCH₂C«CH

TABLE 20

B¹ B^J X B B^ B³ X

CF₃ 6-F 4-F-Ph NH₂ CF₃ 6-F 4-F-Ph NHMe

CF₃ 6-F Me NH₂ CF₃ 6-F Me NHMe

CF3 6-F Et NH₂ CF₃ 6-F Et NHMe

CF₃ 6-F i-Pr NH₂ CF₃ 6-F i-Pr NHMe

CF₃ 7-F 4-F-Ph NH₂ CF₃ 7-F 4-F-Ph NHMe

CF₃ 7-F Me NH₂ CF₃ 7-F Me NHMe

CF₃ 7-F Et NH₂ CF₃ 7-F Et NHMe

CF₃ 7-F i-Pr NH₂ CF₃ 7-F i-Pr NHMe

CF₃ 7-Cl 4-F-Ph NH₂ CF₃ 7-Cl 4-F-Ph NHMe

CF₃ 7-Cl Me NH₂ CF₃ 7-Cl Me NHMe

CF₃ 7-Cl Et NH₂ CF₃ 7-Cl Et NHMe

CF₃ 7-Cl i-Pr NH₂ CF₃ 7-Cl i-Pr NHMe

OCF₃ 6-F 4-F-Ph NH₂ OCF₃ 6-F 4-F-Ph NHMe

OCF3 6-F Me NH₂ OCF₃ 6-F Me NHMe

OCF3 6-F Et NH₂ OCF₃ 6-F Et NHMe

OCF3 6-F i-Pr NH₂ OCF₃ 6-F i-Pr NHMe

OCF3 7-F 4-F-Ph NH₂ OCF₃ 7-F 4-F-Ph NHMe

OCF3 7-F Me NH₂ OCF₃ 7-F Me NHMe

OCF₃ 7-F Et NH₂ OCF₃ 7-F Et NHMe

OCF₃ 7-F i-Pr NH₂ OCF₃ 7-F i-Pr NHMe

OCF₃ 7-Cl 4-F-Ph NH₂ OCF₃ 7-Cl 4-F-Ph NHMe

OCF₃ 7-Cl Me NH₂ OCF₃ 7-Cl Me NHMe

OCF₃ 7-Cl Et NH₂ OCF₃ 7-Cl Et NHMe

OCF₃ 7-Cl i-Pr NH₂ OCF₃ 7-Cl i-Pr NHMe

B¹ B^ B³ B¹ B^z B³ X

C ₃ 6-F 4-F-Ph NH(CO)NHMe CF₃ 6-F 4-F-Ph NHC0₂Me

CF₃ 6-F Me NH(CO)NHMe CF₃ 6-F Me NHC0₂Me

CF₃ 6-F Et NH(CO)NHMe CF₃ 6-F Et NHC0₂Me

CF₃ 6-F i-Pr NH(CO)NHMe CF₃ 6-F i-Pr NHC0₂Me

CF₃ 7-F 4-F-Ph NH(CO)NHMe CF₃ 7-F 4-F-Ph NHC0₂Me

CF₃ 7-F Me NH(CO)NHMe CF₃ 7-F Me NHC0₂Me

CF₃ 7-F Et NH(CO)NHMe CF₃ 7-F Et NHC0₂Me

CF₃ 7-F i-Pr NH(CO)NHMe CF₃ 7-F i-Pr NHC0₂Me

CF₃ 7-Cl 4-F-Ph NH(CO)NHMe CF₃ 7-Cl 4-F-Ph NHC0₂Me

CF₃ 7-Cl Me NH(CO)NHMe CF₃ 7-Cl Me NHC0 Me

CF₃ 7-Cl Et NH(CO)NHMe CF₃ 7-Cl Et NHC0 Me

CF₃ 7-Cl i-Pr NH(CO)NHMe CF₃ 7-Cl i-Pr NHC0₂Me

OCF₃ 6-F 4-F-Ph NH(CO)NHMe OCF₃ 6-F 4-F-Ph NHC0₂Me

OCF₃ 6-F Me NH(CO)NHMe OCF3 6-F Me NHC0₂Me

OCF₃ 6-F Et NH(CO)NHMe OCF3 6-F Et NHCO^e

OCF₃ 6-F i-Pr NH(CO)NHMe OCF3 6-F i-Pr NHC0₂Me

OCF₃ 7-F 4-F-Ph NH(CO)NHMe OCF3 7-F 4-F-Ph NHC0₂Me

OCF₃ 7-F Me NH(CO)NHMe OCF3 7-F Me NHC0₂Me

OCF₃ 7-F Et NH(CO)NHMe OCF3 7-F Et NHC0₂Me

OCF₃ 7-F i-Pr NH(CO)NHMe OCF3 7-F i-Pr NHC0₂Me

OCF₃ 7-Cl 4-F-Ph NH(CO)NHMe OCF3 7-Cl 4-F-Ph NHC0₂Me

OCF₃ 7-Cl Me NH(CO)NHMe OCF3 7-Cl Me NHC0₂Me

OCF₃ 7-Cl Et NH(CO)NHMe OCF3 7-Cl Et NHC0₂Me

OCF₃ 7-Cl i-Pr NH(CO)NHMe OCF3 7-Cl i-Pr NHC0₂Me

B¹ B³ X B¹ B^ B³ X

CF₃ 6-F 4-F-Ph N-CHPh CF₃ 6-F 4-F-Ph OH

CF₃ 6-F Me N-CHPh CF₃ 6-F Me OH

CF₃ 6-F Et N-CHPh CF₃ 6-F Et OH

CF₃ 6-F i-Pr N-CHPh CF₃ 6-F i-Pr OH

CF₃ 7-F 4-F-Ph N-CHPh CF₃ 7-F 4-F-Ph OH

CF₃ 7-F Me N-CHPh C ₃ 7-F Me OH

CF₃ 7-F Et N-CHPh CF₃ 7-F Et OH

CF₃ 7-F i-Pr N-CHPh CF₃ 7-F i-Pr OH

CF₃ 7-Cl 4-F-Ph N-CHPh CF₃ 7-Cl 4-F-Ph OH

CF₃ 7-Cl Me N-CHPh CF₃ 7-Cl Me OH

CF₃ 7-Cl Et N-CHPh CF₃ 7-Cl Et OH

CF₃ 7-Cl i-Pr N-CHPh CF₃ 7-Cl i-Pr OH

OCF₃ 6-F 4-F-Ph N-CHPh OCF₃ 6-F 4-F-Ph OH

OCF₃ 6-F Me N-CHPh OCF₃ 6-F Me OH

OCF₃ 6-F Et N-CHPh OCF₃ 6-F Et OH

OCF₃ 6-F i-Pr N-CHPh OCF₃ 6-F i-Pr OH

OCF₃ 7-F 4-F-Ph N-CHPh OCF₃ 7-F 4-F-Ph OH

OCF₃ 7-F Me N-CHPh OCF₃ 7-F Me OH

OCF₃ 7-F Et N-CHPh OCF₃ 7-F Et OH

OCF₃ 7-F i-Pr N-CHPh OCF₃ 7-F i-Pr OH

OCF₃ 7-Cl 4-F-Ph N-CHPh OCF₃ 7-Cl 4-F-Ph OH

OCF₃ 7-Cl Me N-CHPh OCF₃ 7-Cl Me OH

OCF₃ 7-Cl Et N-CHPh OCF₃ 7-Cl Et OH

OCF₃ 7-Cl i-Pr N-CHPh OCF₃ 7-Cl i-Pr OH

B^x B³ X

CF₃ 6-F 4-F-Ph OMe

CF₃ 6-F Me OMe

CF₃ 6-F Et OMe

CF₃ 6-F i-Pr OMe

CF₃ 7-F 4-F-Ph OMe

CF₃ 7-F Me OMe

C ₃ 7-F Et OMe CF₃ 7-F i-Pr OMe