Hydrochloric Acid → HCID 178523533, compound

Participants

Reaction Steps

DIPEA (88 mg, 0.68 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (36 mg, 0.15 mmol) in DMF (1 mL) followed by HOBt (20 mg, 0.15 mmol) and EDCI.HCl (39 mg, 0.2 mmol). After 2 minutes 4-(2-trifluoromethyl-benzenesulfonyl)-piperidine hydrochloride (250 mg, 1.0 mmol) (prepared from 4-(2-trifluoromethyl-phenylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester by means of oxidation with hydrogen peroxide and subsequent hydrolysis of the N-protection group with hydrochloric acid) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected. The solid obtained was purified by column chromatography (using 60-120 silica gel and 5% MeoH in DCM as eluent) to afford 21 mg (29.6% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzenesulfonyl)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 521.14, 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.2 (m, 5H), 7.7 (d, 2H), 7.5-7.3 (m, 3H), 7.1 (s, 1H), 4.5 (d, 1H), 4.2-4.0 (m, 2H), 4.0 (d, 1H), 3.7-3.5 (t, 1H), 3.1 (t, 1H), 2.7 (m, 1H), 1.9-1.7 (m, 2H), 1.7 (m, 1H), 1.5 (m, 1H).

Provenance & Evidence