1-Hydroxybenzotriazole → HCID 178523526, compound

Participants

Reaction Steps

DIPEA (387 mg, 3.0 mmol) was added a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (247 mg, 1.0 mmol) in DMF (2 mL) followed by HOBt (162 mg, 1.2 mmol) and EDCI.HCl (229 mg, 1.2 mmol). After 2 minutes 3-chloro-5-(piperidin-4-yloxy)-pyridine hydrochloride (prepared according to the method used for the synthesis of Intermediate 15) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate and dried over sodium sulfate. The organic layer was concentrated under reduced pressure. Purification by column chromatography (using 60-120 silica gel and 5% MeoH in CHCl3 as eluent) to afford 56 mg (12.71% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 440.14, 95.7%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.2 (m, 2H), 8.0 (m, 1H), 7.8 (m, 3H), 7.4 (m, 4H), 7.1 (m, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 3.9 (m, 1H), 3.8 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 2.0 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence