HCID 24701836, compound → HCID 178523377, compound

Participants

Reaction Steps

A suspension of 212 mg (0.84 mmol) of 5-amino-2-chloro-N-(2,2,2-trifluoroethyl)benzamide and 168 mg (1.26 mmol) of silver(I) cyanide in 5.0 ml of dichloromethane is admixed with a solution of 265 mg (0.84 mmol) of 3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride in 3.0 ml of dichloromethane and stirred for 16 h at room temperature. The suspension is then filtered over silica gel and the product is eluted with a mixture of dichloromethane and methanol (1:1). The solvents are removed under reduced pressure on a rotary evaporator and the resulting crude product is taken up in ethyl acetate. The organic phase is washed successively twice with 1M hydrochloric acid and once with saturated sodium chloride solution. The organic phase is then dried over magnesium sulphate, filtered and concentrated by evaporation under reduced pressure on a rotary evaporator. The crude product is then triturated with a mixture of dichloromethane, methyl tert-butyl ether and cyclohexane (1:1:1). The crude product obtained from the mother liquor is then purified by means of preparative HPLC. In this way, 49 mg of N-{4-chloro-3-[(2,2,2-trifluoroethyl)carbamoyl]phenyl}-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (11%) were obtained as a colourless solid.

Provenance & Evidence