1-Hydroxybenzotriazole → HCID 178425532, compound

Participants

Reaction Steps

DIPEA (426 mg, 3.3 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (285 mg, 1.1 mmol) in DMF (3 mL) followed by HOBt (175 mg, 1.3 mmol) and EDCI.HCl (252 mg, 1.3 mmol). After 2 minutes 4-methyl-3-(piperidin-4-ylamino)-benzonitrile dihydrochloride (250 mg, 1.1 mmol) (prepared according to the method used for the synthesis of Intermediate 3) was added and the 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) afforded 100 mg (22.7% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(5-cyano-2-methyl-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 443.31, 91.96%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.1 (t, 1H), 7.8 (d, 2H), 7.4 (m, 4H), 7.2 (m, 2H), 7.0 (s, 1H), 6.9 (d, 1H), 5.0 (d, 1H), 4.4 (m, 1H), 4.2 (m, 2H), 3.9 (m, 1H), 3.7 (m, 1H), 3.2 (m, 1H), 2.8 (m, 1H), 2.2 (s, 3H), 2.0 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence