4-Methylmorpholine → HCID 178513629, compound

Participants

Reaction Steps

N-Methyl morpholine (28 mg, 0.28 mmol) was added to a cold (−70° C.) solution of 2-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid (100 mg, 0.2 mmol) in THF (2 mL) followed by isobutyl chloroformate (41 mg, 0.3 mmol) and stirring was continued at the at −70° C. for 1 hr. After complete formation of anhydride, ammonia gas was bubbled through the reaction mixture at −70° C. for 10 minutes. The resulting mixture was then stirred at room temperature for 1 hr. Water (10 mL) was added, the precipitated was filtered and dried to afford 54 mg (60.6% yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-carbamoyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 448.18, 93.4%. 1H NMR (300 MHz, DMSO-d6): δ 7.9 (m, 1H), 7.8 (m, 2H), 7.5 (m, 3H), 7.4 (m, 1H), 7.3 (m, 1H), 7.1 (m, 2H), 4.3 (s, 2H), 4.0 (m, 1H), 3.8 (m, 1H), 3.5 (m, 2H), 2.1 (m, 3H), 1.9 (m, 3H), 1.1 (m, 1H).

Provenance & Evidence