Water → HCID 49853688, compound

Participants

Reaction Steps

To a solution of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 30 mg, 0.074 mmol) and triethylamine (70 mg, 0.69 mmol) in dichloromethane (6 ml) was added cinnamoyl chloride (18 mg, 148 mmol) at 0° C. The reaction was stirred at RT for 3 hours. The reaction mixture was poured into cold water and organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain title compound. 1H NMR (CDCl3, 300 MHz): δ 9.921 (s, 1H), 8.204-8.257(d, 1H ,J=15.9 Hz), 8.071-8.123 (d, 1H,J=15.6 Hz), 7.983-8.013 (d, 1H J=9 Hz), 7.806-7.834 (d, 2H, J=8.4 Hz), 7.63-7.68 (m, 3H), 7.569-7.597 (d, 2H,J=8.4 Hz), 7.396-7.412 (m, 3H), 7.059-7.066 (d, 1H, J=2.1 Hz), 1.858 (s, 6H); MS: m/z 539 (M+).

Provenance & Evidence