1-Hydroxybenzotriazole → HCID 178485311, compound

Participants

Reaction Steps

DIPEA (72 mg, 0.56 mmol) was added to a stirred solution of 2-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid (75 mg, 0.16 mmol) in DMF (2 mL) followed by HOBt (33 mg, 0.24 mmol) and EDCI.HCl (46 mg, 0.24 mmol). After 2 minutes of stirring, methyl amine hydrochloride (11 mg, 0.16 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated The residue was purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3) afford 23 mg (31.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-methylcarbamoyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 462.2, 96.9%. 1H NMR (300 MHz, DMSO-d6): δ 8.1 (m, 1H), 8.0 (m, 1H), 7.8 (m, 2H), 7.6 (m, 1H), 7.4 (m, 4H), 7.2 (m, 1H), 7.1 (b, 1H), 7.0 (m, 1H), 4.8 (b, 1H), 4.2 (m, 2H), 3.6 (m, 3H), 2.8 (d, 3H), 2.0 (m, 2H), 1.8 (m, 2H).

Provenance & Evidence