1-Hydroxybenzotriazole → HCID 178523529, compound

Participants

Reaction Steps

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.15 g, 0.000533 mol) in DMF (3 mL) was added DIPEA (0.206 g, 0.00160 mol), HOBt (0.0864 g, 0.00064 mol) and EDCI.HCl (0.122 g, 0.00064 mol) at ambient temperature. After 2 minutes 4-(2-bromo-phenylsulfanyl)-piperidine hydrochloride (0.197 g, 0.00064 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. Purification by column chromatography using silica gel 60-120 mesh (40% ethyl acetate in hexane) afforded 0.097 g (36%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-phenylsulfanyl)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 499.07 (M+1)+, 95.7%, 1H NMR (DMSO-d6): δ 13.8 (d, 1H), 8.1 (t, 1H), 7.8 (d, 2H), 7.6 (dd, 1H), 7.58-7.3 (m, 6H), 7.22-7.06 (m, 2H), 4.3-4.1 (m, 3H), 3.9-3.6 (m, 2H), 3.0 (m, 1H), 2.0 (m, 2H), 1.7-1.4 (m, 3H).

Provenance & Evidence