1-Hydroxybenzotriazole → HCID 178523524, compound

Participants

Reaction Steps

DIPEA (540 mg, 4.2 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (344 mg, 1.4 mmol) in DMF (3 mL) followed by HOBt (229 mg, 1.7 mmol) and EDCI.HCl (321 mg, 1.7 mmol). After 2 minutes 2-amino-1-[4-(pyridin-4-yloxy)-piperidin-1-yl]-ethanone hydrochloride (250 mg, 1.4 mmol) (prepared according to Step 1 and 5 of the General Scheme) 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 198 mg (% 34.9 Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(pyridin-4-yloxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 406.18, 95.8%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.4 (m, 2H), 8.1 (m, 1H), 7.8 (m, 2H), 7.1 (m, 1H), 7.0 (s, 2H), 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), 1.7 (m, 2H).

Provenance & Evidence