Dimethylamine → HCID 68773078, compound

Participants

Reaction Steps

To a solution of 2-[10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-1-yl]-5-methylbenzaldehyde (50.0 mg, 0.122 mmol) in tetrahydrofuran (0.5 mL) and ethanol (0.5 mL) was added dimethylamine (2.0 M solution in tetrahydrofuran, 305 μL, 0.610 mmol). The reaction mixture was stirred at room temperature for 12 hr. To the mixture were added sodium borohydride (9.23 mg, 0.244 mmol) and titanium tetraisopropoxide (72.0 μL, 0.244 mmol). The reaction mixture was stirred at room temperature for 9 hr. The reaction mixture was quenched with aqueous ammonia at 0° C. and extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 0-20% ethyl acetate/n-hexane gradient mixture. The residue was dissolved into ethyl acetate and 4.0 M hydrochloric acid in ethyl acetate was added (0.20 mL) to the solution. The mixture was stirred for 5 min, and concentrated in vacuo to give the title compounds as an amorphous (30.0 mg, 0.0631 mmol, 52%).

Provenance & Evidence