1-Hydroxybenzotriazole → HCID 178428400, compound

Participants

Reaction Steps

DIPEA (154 mg, 1.4 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (107 mg, 0.4 mmol) in DMF (2 mL) followed by HOBt (54 mg, 0.4 mmol) and EDCI.HCl (84 mg, 0.44 mmol). After 2 minutes 4-methyl-3-(piperidin-4-yloxy)-pyridine hydrochloride (100 mg, 0.4 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, the solid collected. Purification of the solid by washing with 10% MeOH in CHCl3 afforded 106 mg (66% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(4-methyl-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 420, 98.9%. 1H NMR (300 MHz, DMSO-d6): δ 14.0 (b, 1H), 8.6 (s, 1H), 8.4 (d, 1H), 8.2 (b, 1H), 7.8 (m, 3H), 7.5 (m, 2H), 7.4 (m, 1H), 7.2 (s, 1H), 4.9 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.4 (s, 3H), 2.0 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence