Dimethylamine → HCID 57786180, compound

To a solution of 3-chloro-4-[8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazol-1-yl]benzaldehyde (68.3 mg, 0.170 mmol) in tetrahydrofuran (0.5 mL) and ethanol (0.5 mL) were added dimethylamine (2.0 M solution in tetrahydrofuran, 850 μL, 1.70 mmol) and titanium tetraisopropoxide (100.0 μL, 0.340 mmol). The reaction mixture was stirred at room temperature for 16 hr. To the mixture was added sodium triacetoxyborohydride (72.1 mg, 0.340 mmol) and the reaction mixture was stirred at room temperature for 5 hr. The reaction mixture was warmed to 40° C. and stirred for 3 hr. To the mixture were added sodium triacetoxyborohydride (360.0 mg, 1.70 mmol) and dimethylamine (2.0 M solution in tetrahydrofuran, 425 μL, 0.85 mmol). The reaction mixture was stirred at 40° C. for 0.5 hr. The reaction mixture was quenched with water 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 silica gel column chromatography eluting with a 0-100% ethyl acetate/n-hexane gradient mixture to give the title compound as an amorphous (32.5 mg, 0.0753 mmol, 44%).

1. stirringthe reaction mixture was stirred at room temperature for 5 hr
2. temperatureThe reaction mixture was warmed to 40° C.
3. stirringstirred for 3 hr
4. stirringThe reaction mixture was stirred at 40° C. for 0.5 hr
5. customThe reaction mixture was quenched with water
6. extractionextracted with ethyl acetate (×3)
7. washThe combined organic layer was washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe residue was purified by silica gel column chromatography
12. washeluting with a 0-100% ethyl acetate/n-hexane gradient mixture

ORD record

ord-962164df79c5464aab0c27c01321037f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785460B2