Trimethylsilyl isocyanate → 4-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid amide

Participants

Reaction Steps

To a solution of 4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-1-piperidin-4-ylmethyl-piperazin-2-one (20 mg, 0.047 mmol) in a mixture of 1,2-dichloroethane (1 mL) and THF (1 mL) is added trimethylsilyl isocyanate (0.006 mL, 0.05 mmol) and stirred 60 hours. The reaction is concentrated and purified by column chromatography (silica, 20% methanol/dichloromethane) to provide 4-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid amide. 1H NMR (300 MHz, CD3OD) d 8.09 (s, 1H), 8.02 (d, 2H), 7.53 (dd, 1H), 3.90 (d, 4H), 3.49 (d, 4H), 3.30-3.24 (m, 2H), 2.65 (dt, 2H), 1.49 (d, 2H), 1.12-0.97 (m, 2H); MS (Ion spray) 471 (M+H).

Provenance & Evidence