HCID 57991631, compound → HCID 57991638, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 ml three-necked flask were added 0.60 g (1.43 mmol) N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-4-fluoro-benzamide prepared in Example 4 and 15 ml dichloromethane, maintaining the temperature at lower than −10° C. in ice salt bath, and then added dropwise 1.7 ml of 1.763 mol/L BBR3 solution in dichloromethane. Upon the completion of addition, the resulting mixture was stirred at that temperature for 1 hour and then at room temperature for 1 hour, added 2 g ice, distilled under a reduced pressure to remove dichloromethane, and then added 20 ml ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under a reduced pressure to give a crude product, which was recrystallized with ethyl acetate/petroleum ether to obtain a 0.39 product as a white solid in a yield of 67.2%, mp: 205-206 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.22 (2H, s, CH2), 6.84 (2H, d, J=8.68 Hz, ArH), 7.23˜7.39 (7H, m, ArH), 7.47 (2H, d, J=8.68 Hz, ArH), 8.15 (2H, dd, 3JHH=9.00, 4JFH=5.64 Hz, ArH), 9.62 (1H, s, OH), 12.66 (1H, s, CONH); EI-MS m/e (%): 404.1 (M+, 100), 123.0 (70); HREI-MS Calcd. for C23H17FN2O2S: 404.0995. found: 404.0988.

Provenance & Evidence