Dimethylamine → HCID 68776254, 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-(trifluoromethoxy)benzaldehyde (48.9 mg, 0.102 mmol) in tetrahydrofuran (0.5 mL) and ethanol (0.2 mL) was added dimethylamine (2.0 M solution in tetrahydrofuran, 250 μL, 0.509 mmol). The reaction mixture was stirred at room temperature for 14 hr. To the mixture were added anhydrous sodium borohydride (46.2 mg, 1.22 mmol) and titanium tetraisopropoxide (60.3 μL, 0.204 mmol). The reaction mixture was stirred at room temperature for 9 hr and warmed to 40° C. and stirred for 14 hr. The reaction mixture was quenched with aqueous ammonia at 0° C. The precipitate was filtered and the filtrate was extracted with ethyl acetate (×3). The combined organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by basic silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture. The residue was dissolved into ethyl acetate and to the solution was added 4.0 M hydrochloric acid in ethyl acetate (0.20 mL), and the mixture was stirred for 5 min, and concentrated in vacuo to give the title compounds as a colorless amorphous (38.1 mg, 0.0698 mol, 69%).

Provenance & Evidence