Hydrochloric Acid → HCID 66881382, compound

The compound (16.1 g, 53.1 mmol) of step A was dissolved in N,N-dimethylformamide (200 ml), 60% sodium hydride (2.41 g, 60.3 mmol) was added under ice-cooling with stirring, and the mixture was stirred at 0° C. for 45 min. Then, methyl iodide (5.0 ml, 80.3 mmol) was added, and the mixture was stirred at the same temperature for 100 min. To the reaction mixture was added diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated. The obtained solid was purified by silica gel column chromatography (hexane:dichloromethane:ethyl acetate-10:1:1) to give the title compound (6.09 g, yield 36%) as a yellow solid.

1. temperaturecooling
2. stirringthe mixture was stirred at 0° C. for 45 min
3. stirringthe mixture was stirred at the same temperature for 100 min
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe solution was concentrated
9. customThe obtained solid was purified by silica gel column chromatography (hexane:dichloromethane:ethyl acetate-10:1:1)

ORD record

ord-4fb3c59bb09e44baacbfb52390f1611a

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2