4-Toluenesulfonyl chloride → 5-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carbonitrile

Participants

Reaction Steps

Combine 5-Amino-1-(3,5-bis-trifluoromethyl-benzyl)-1H-imidazole-4-carboxylic acid amide (0.106 g, 0.30 mmol) and p-toluenesulfonyl chloride (0.069 g, 0.36 mmol) in pyridine (0.1 M), and stir at RT. After 2 h, quench the reaction with MeOH and concentrate. Redissolve in EtOAc, wash with H2O and brine, then dry (MgSO4), filter, and concentrate. Purify by radial chromatography on silica gel to give the title compound. MS (ES) 335.1 (M+1); 1H NMR (300 MHz, CD3OD): δ 7.96 (s, 1H), 7.77 (s, 2H), 7.37 (s, 1H), 5.31 (s, 2H).

Provenance & Evidence