OTAVA-BB 1287452

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.16 g (5 mmol) of N-(3,5-dichloro,α,α-dimethylbenzyl)formamide and 8 ml of 2N hydrochloric acid was refluxed for 30 minute. After cooling, the reaction solution was alkalified with a sodium hydroxide aqueous solution and extracted with diethyl ether. The ether solution was washed with water, dried and then concentrated to obtain 1.0 g (yield: 98.0%) of the desired compound. was refluxed for 30 minute After cooling extracted with diethyl ether The ether solution was washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 70.0 mg (0.238 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 48.6 mg (0.238 mmol) of 2-(3,5-dichlorophenyl)propan-2-amine are placed in 2 ml of dimethylformamide and treated with 38.6 mg (0.286 mmol) of HOBt. After 10 mins' stirring, 59.4 mg (0.310 mmol) of EDC hydrochloride are added and the mixture is stirred overnight at room temperature. Without further workup, the mixture is purified directly by preparative HPLC [Method 10]. 70 mg (61% of theory) of the target compound are thus obtained. the mixture is stirred overnight at room temperature Without further workup, the mixture is purified directly by preparative HPLC [Method 10] 70 mg (61% of theory) of the target compound are thus obtained

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methyl-1-(3,5-dichlorophenyl)ethylamine (7.5 g) was added slowly to formalin (aqueous 37% HCHO solution) (4.6 g) at room temperature. This was allowed to react as it was for 7 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, which was then extracted with ether. After it was washed with saturated saline, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the captioned compound (8.6 g) as white crystals. to react as it was then extracted with ether After it was washed with saturated saline the organic layer was dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.16 g (5 mmol) of N-(3,5-dichloroα,α-dimethylbenzyl)formamide and 8 ml of 2N hydrochloric acid was refluxed for 30 minutes. After cooling, the reaction solution was alkalified with a sodium hydroxide aqueous solution and extracted with diethyl ether. The ether solution was washed with water, dried and then concentrated to obtain 1.0 g (yield: 98.0%) of the desired compound. was refluxed for 30 minutes After cooling extracted with diethyl ether The ether solution was washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Methyl-1-(3,5-dichlorophenyl)ethylamine (7.5 g) was gradually added to formalin (37% aqueous HCHO solution) (4.6 g) at room temperature. This mixture was subjected as it is to reaction for 7 hours. A saturated sodium bicarbonate solution was added to the reaction mixture, the resultant was extracted with ether and this organic layer was washed with saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to obtain 8.6 g of N-methylene-1-methyl-1-(3,5-dichloro-phenyl)ethylamine as white crystals. is to reaction for 7 hours the resultant was extracted with ether this organic layer was washed with saturated saline solution dried over anhydrous sodium sulfate The solvent was removed by evaporation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.16 g (5 mmol) of N-(3,5-dichloro,α,α-dimethylbenzyl)formamide and 8 ml of 2N hydrochloric acid was refluxed for 30 minute. After cooling, the reaction solution was alkalified with a sodium hydroxide aqueous solution and extracted with diethyl ether. The ether solution was washed with water, dried and then concentrated to obtain 1.0 g (yield: 98.0%) of the desired compound. was refluxed for 30 minute After cooling extracted with diethyl ether The ether solution was washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 70.0 mg (0.238 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 48.6 mg (0.238 mmol) of 2-(3,5-dichlorophenyl)propan-2-amine are placed in 2 ml of dimethylformamide and treated with 38.6 mg (0.286 mmol) of HOBt. After 10 mins' stirring, 59.4 mg (0.310 mmol) of EDC hydrochloride are added and the mixture is stirred overnight at room temperature. Without further workup, the mixture is purified directly by preparative HPLC [Method 10]. 70 mg (61% of theory) of the target compound are thus obtained. the mixture is stirred overnight at room temperature Without further workup, the mixture is purified directly by preparative HPLC [Method 10] 70 mg (61% of theory) of the target compound are thus obtained