1-Hydroxybenzotriazole → HCID 178523516, compound

Participants

Reaction Steps

DIPEA (271 mg, 2.1 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (162 mg, 0.7 mmol) in DMF (2 mL) followed by HOBt (94 mg, 0.7 mmol) and EDCI.HCl (134 mg, 0.7 mmol). After 2 minutes 2-chloro-6-(piperidin-4-yloxy)-pyridine hydrochloride (prepared according to the method used for the synthesis of Intermediate 15) (140 mg, 0.7 mmol) 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) afforded 53 mg (18.27% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(6-chloro-pyridin-2-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 440.14, 90%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.2 (b, 1H), 7.8 (m, 3H), 7.4 (m, 3H), 7.1 (m, 1H), 6.8 (m, 1H), 5.2 (m, 1H), 4.2 (m, 2H), 3.8 (m, 1H), 3.7 (m, 1H), 3.5 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence