1-Hydroxybenzotriazole → HCID 178497862, compound

Participants

Reaction Steps

DIPEA (423 mg, 2.4 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (200 mg, 0.81 mmol) in DMF (3 mL) followed by HOBt (130 mg, 0.93 mmol) and EDCI.HCl (187 mg, 0.93 mmol). After 2 minutes 4-methyl-3-(piperidin-4-yloxy)-benzoic acid methyl ester hydrochloride (prepared according to the method used for the synthesis of Intermediate 15) (280 mg, 0.97 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 to afford 266 mg (68.55% Yield) of 4-methyl-3-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid methyl ester. LC/MS [M+H]+: 477.21, 96.63%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.1-8.0 (m, 1H), 7.8 (d, 2H), 7.54-7.28 (m, 6H), 7.1 (bs, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.8 (s, 3H), 3.8-3.6 (m, 2H), 3.6-3.4 (m, 2H), 2.2 (s, 3H), 2.1-1.8 (m, 2H), 1.8-1.5 (m, 2H).

Provenance & Evidence