Acetyl chloride → N-acetyl-2-[4-(Benzyloxy)phenyl]-1-cyclohexyl-1H-benzimidazol-5-sulfonamide

Participants

Reaction Steps

A solution of intermediate 69 (0.023 g, 0.05 mmol) in N,N-dimethylformamide (0.200 mL) and lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran) (0.050 ml, 0.05 mmol) was cooled to 0° C. Acetyl chloride (0.005 ml, 0.06 mmol) was added. The reaction mixture was stirred at rt for 1.5 h. At this time, more lithium bis(trimethylsilyl)amide solution (0.050 ml, 0.05 mmol) and acetyl chloride (0.010 ml, 0.014 mmol) were added. The reaction was stirred at rt overnight and concentrated. The crude material was purified by reverse phase HPLC (C18 column, water/acetonitrile gradient containing 0.05% trifluoroacetic acid) to afford the product as a white solid (0.006 g, 18%). 1H NMR (CDCl3) δ 8.52 (br s, 1H), 8.15 (br s, 1H), 7.84 (br m, 1H), 7.61 (br m, 2H), 7.47-7.29 (br m, 5H), 7.22 (br m, 2H), 5.18 (s, 2H), 4.46 (m, 1H), 2.30 (br m, 4H), 2.01 (br m, 2H), 1.82 (br m, 1H), 1.37 (br m, 3H); ESI-MS m/e 504.1 (M+1); HPLC purity (ELSD) 100%.

Provenance & Evidence