1-Hydroxybenzotriazole → HCID 178432687, compound

Participants

Reaction Steps

DIPEA (193 mg, 1.5 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (127 mg, 0.5 mmol) in DMF (2 mL) followed by HOBt (67 mg, 0.5 mmol) and EDCI.HCl (105 mg, 0.55 mmol). After 2 minutes 2-methyl-3-(piperidin-4-yloxy)-pyridine hydrochloride (100 mg, 0.5 mmol) (prepared by 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, and the solid was collected. Purification of the solid by washing with 10% MeOH in CHCl3 afforded 95 mg (47.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-methyl-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 420, 96.7%. 1H NMR (300 MHz, DMSO-d6): δ 8.3 (m, 1H), 8.2 (b, 1H), 8.0 (m, 1H), 7.8 (m, 2H), 7.6 (m, 1H), 7.5 (m, 2H), 7.4 (m, 1H), 7.2 (b, 1H), 4.9 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.5 (m, 3H), 2.0 (m, 2H), 1.8 (m, 2H).

Provenance & Evidence