1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874401, compound

Participants

Reaction Steps

DIPEA (167.9 mg, 1.3 mmol) was added to a stirred solution of [(1-phenyl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (80 mg, 0.32 mmol) in DMF (3 mL) followed by HOBt (48.2 mg, 0.35 mmol) and EDCI (124.5 mg, 0.65 mmol). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (77.5 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and precipitate was collected. The solid was purified by column chromatography (using 70% ethyl acetate in hexane as eluent) to afford 45 mg (32.6% Yield) of 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 431.18, 85.06%. 1H NMR (300 MHz, DMSO-d6): δ 9.35 (s, 1H), 8.5 (t, 1H), 8.0 (d, 2H), 7.7-7.6 (m, 2H), 7.58-7.45 (m, 3H), 7.45-7.32 (m, 2H), 4.75 (m, 1H), 4.2 (d, 2H), 4.0-3.9 (m, 1H), 3.8-3.7 (m, 1H), 2.1-1.9 (m, 2H), 1.75-1.5 (m, 2H).

Provenance & Evidence