1-Hydroxybenzotriazole → HCID 178523530, compound

Participants

Reaction Steps

To a stirred solution of [(5-Phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.05 g, 0.00018 mol) in DMF (1 mL) was added DIPEA (0.0689 g, 0.00053 mol), HOBt (0.028 g, 0.00021 mol) and EDCI.HCl (0.0407 g, 0.00021 mol) at ambient temperature. After 2 minutes 4-(2-trifluoromethyl-phenylsulfanyl)-piperidine hydrochloride (0.063 g, 0.00021 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried to afford 0.068 g (78%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylsulfanyl)-piperidin-1-yl]-ethyl}-amide. LCMS: 489.15 (M+1)+, 94.5%, 1H NMR (DMSO-d6): δ 13.8 (s, 1H), 8.0 (s, 1H), 7.8 (m, 4H), 7.65 (t, 1H), 7.5-7.3 (m, 4H), 7.1 (s, 1H), 4.3-4.05 (m, 3H), 3.9-3.6 (m, 2H), 3.2 (m, 1H), 2.9 (m, 1H), 1.9 (m, 2H), 1.6 (m, 1H), 1.4 (m, 1H).

Provenance & Evidence