Toluene → HCID 86710170, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(1H-imidazol-2-yl)benzofuran-6-yl)-N-(4-hydrazinyl-4-oxobutyl)methanesulfonamide (13 mg, 0.025 mmol) in anhydrous CHCl3 (400 μL) and anhydrous tetrahydrofuran (400 μL) was added 20 wt % phosgene in toluene (66.9 μL, 0.127 mmol) under nitrogen, and the mixture was heated at reflux in an oil bath at 85° C. for 30 minutes. The reaction was cooled to room temperature and concentrated by rotary evaporation to a white solid. The crude material was purified by SiO2 flash chromatography (Alltech Extract-Clean™ column, 5 g bed) eluting with 5% methanol/CH2Cl2 to afford the title compound as a white solid (10 mg, 0.018 mmol, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.50-0.60 (m, 1H), 0.80-0.93 (m, 1H), 0.99 (d, J=8.57 Hz, 2H), 1.69-1.85 (m, 2H), 2.34-2.43 (m, 1H), 2.59-2.66 (m, 2H), 3.17 (s, 3H), 3.66-3.87 (m, 2H), 7.09 (s, 1H), 7.18 (s, 1H), 7.26-7.45 (m, 3H), 7.88 (s, 1H), 8.02 (dd, J=8.89, 5.53 Hz, 2H), 11.99 (br s, 1H), 12.41 (s, 1H); MS (ESI+) m/z 538 (M+H)+, 1075 (2M+H)+; MS (ESI−) m/z 536 (M−H)−, 1073 (2M−H)−.

Provenance & Evidence