1-Hydroxybenzotriazole → HCID 178466199, compound

Participants

Reaction Steps

DIPEA (232 mg, 1.8 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (144 mg, 0.6 mmol) in DMF (2 mL) followed by HOBt (97 mg, 0.7 mmol) and EDCI.HCl (137 mg, 0.7 mmol). After 2 minutes 1-[2-(piperidin-4-yloxy)-phenyl]-ethanone dihydrochloride (prepared according to Step 1 and 5 of the General Scheme) (150 mg, 0.6 mmol) was added 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. Purification by column chromatography (using 60-120 silica gel and 5% MeoH in CHCl3 as eluent) to afford 112 mg (50.9% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-acetyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 447.2, 95.68%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.2 (bs, 1H), 7.8 (d, 2H), 7.5 (m, 4H), 7.4 (m, 1H), 7.3 (m, 1H), 7.2 (s, 1H), 7.0 (t, 1H), 4.8 (m, 1H), 4.4 (m, 2H), 3.8 (m, 1H), 3.4 (m, 1H), 3.5 (m, 2H), 2.5 (s, 3H), 2.0 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence