1-Hydroxybenzotriazole → HCID 178519541, compound

Participants

Reaction Steps

DIPEA (360 mg, 2.8 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (190 mg, 0.8 mmol) in DMF (2.0 mL) followed by HOBt (160 mg, 1.2 mmol) and EDCI.HCl (230 mg, 1.2 mmol). After 2 minutes of stirring, 2-(piperidin-4-yloxy)-benzaldehyde hydrochloride (200 mg, 0.8 mmol) (prepared according to Step 1 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 150 mg (44% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-formyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 433.18, 98.8%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 10.3 (s, 1H), 8.2 (m, 1H), 7.8 (m, 2H), 7.7 (m, 2H), 7.5 (m, 2H), 7.4 (m, 2H), 7.1 (m, 2H), 5.0 (m, 1H), 4.2 (m, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H).

Provenance & Evidence