1-Hydroxybenzotriazole → HCID 178523507, compound

Participants

Reaction Steps

DIPEA (360 mg, 2.8 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (200 mg, 0.8 mmol) in DMF (2 mL) followed by HOBt (131 mg, 0.97 mmol) and EDCI.HCl (187 mg, 00.97 mmol). After 2 minutes of stirring, 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (200 mg, 0.8 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (using neutral alumina and 5% MeOH in CHCl3 as eluent) to afford 62 mg (16.2% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 473.17, 91%, 1H NMR (300 MHz, DMSO-d6): δ8.1 (m, 1H), 7.8 (d, 2H), 7.5 (m, 3H), 7.4 (m, 4H), 7.1 (s, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.8 (m, 1H), 3.6 (m, 1H), 3.5 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence