1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66591602, compound

Participants

Reaction Steps

DIPEA (236 mg, 1.826 mmol) was added to a stirred solution of [(1-phenyl-1H-imidazole-4-carbonyl)-amino]-acetic acid (prepared from Intermediate 68 by means of Step 3 of the General Scheme) (100 mg, 0.4 mmol) in DMF (5 mL) followed by HOBt (60.5 mg, 0.4 mmol) and EDCI (195 mg, 1.02 mmol). After 2 minutes of stirring, 4-methyl-3-(piperidin-4-yloxy)-benzonitrile hydrochloride (113 mg, 0.45 mmol) (prepared by the method used for the synthesis of Intermediate 15) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water, the precipitate was collected and purified by recrystallisation from a mixture of diethyl ether (15 mL) and MeOH (0.1 mL) to afford 149 mg (82.7% Yield) of 1-phenyl-1H-imidazole-4-carboxylic acid {2-[4-(5-cyano-2-methyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 443, 98.73%. 1H NMR (300 MHz, DMSO-d6): δ 8.4 (s, 1H), 8.3 (s, 1H), 8.08 (t, 1H), 7.8 (d, 2H), 7.6 (t, 3H), 7.4-7.18 (m, 3H), 4.85 (m, 1H), 4.2 (d, 2H), 3.85-3.6 (d, 2H), 3.5 (bs, 2H), 2.3 (s, 3H), 2.1 (d, 2H), 1.8 (d, 2H).

Provenance & Evidence