1-Hydroxybenzotriazole → HCID 178509670, compound

Participants

Reaction Steps

DIPEA (1.3 g, 0.01 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (720 mg, 2.9 mmol) in DMF (4 mL) followed by HOBt (459 mg, 3.4 mmol) and EDCI.HCl (664 mg, 3.4 mmol). After 2 minutes of stirring, 2-[1-(2-amino-acetyl)-piperidin-4-yloxy]-benzonitrile hydrochloride (prepared by method used for the synthesis of Intermediate 15) (600 mg, 2.9 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (using neutral alumina and 5% MeOH in CHCl3 as eluent) afforded 87 mg (6% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 430.18, 96.4%, 1H NMR (300 MHz, DMSO-d6): δ8.0 (m, 1H), 7.8 (m, 3H), 7.2 (m, 1H), 7.4 (m, 4H), 7.2 (m, 2H), 4.9 (m, 1H), 4.2 (bs, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence