1-Hydroxybenzotriazole → HCID 178509833, compound

Participants

Reaction Steps

DIPEA (135 mg, 1.0 mmol) was added to a stirred of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (150 mg, 0.7 mmol) in DMF (4 mL) followed by HOBt (108 mg, 0.8 mmol) and EDCI.HCl (160 mg, 0.8 mmol). After 2 minutes of stirring 3-(piperidin-4-ylamino)-benzonitrile dihydrochloride (prepared according to Step 2 and 5 of the General Scheme) 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) to afford 91 mg (42% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(3-cyano-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 429.2, 92.9%, 1H NMR (300 MHz, DMSO-d6): δ 8.0 (m, 1H), 7.8 (m, 2H), 7.5 (m, 2H), 7.4 (m, 1H), 7.2 (m, 1H), 7.1 (b, 1H), 6.9 (m, 2H), 6.2 (m, 1H), 4.3 (m, 1H), 4.2 (m, 1H), 3.8 (m, 1H), 3.6 (m, 1H), 3.4 (m, 1H), 2.8 (m, 1H), 2.0 (m, 2H), 1.4 (m, 1H), 1.2 (m, 1H).

Provenance & Evidence