Acetaldehyde → HCID 68773304, compound

Participants

Reaction Steps

To a solution of methyl 5-{7-amino-2-[(2,4-dichlorophenyl)amino]-1H-benzimidazol-1-yl}pentan-1-ol (Reference Example 112; 308 mg, 1.85 mmol) in methanol (8 mL) and acetic acid (0.160 mL) was added acetaldehyde (0.304 mL, 4.88 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium acetoxyborohydride (1.03 g, 4.86 mmol) at 0° C. After the resultant mixture was stirred at room temperature for 14 hr, the mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give the title compound as a solid (317 mg, 0.729 mmol, 90%).

Provenance & Evidence