Dimethylformamide → HCID 66880540, compound

The compound (8.03 g, 24.8 mmol) obtained in step D was added to dichloromethane (160 ml), oxalyl chloride (3.0 ml, 35 mmol) and a catalytic amount of N,N-dimethylformamide were added under ice-cooling with stirring, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, dissolved in tetrahydrofuran (100 ml), 28% aqueous ammonia (20 ml) was added under ice-cooling with stirring, and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (8.77 g) as a colorless solid.

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 2 hr
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. dissolutiondissolved in tetrahydrofuran (100 ml)
5. addition28% aqueous ammonia (20 ml) was added under ice-
6. temperaturecooling
7. stirringwith stirring
8. stirringthe mixture was stirred at the same temperature for 1 hr
9. additionThe reaction mixture was diluted with ethyl acetate
10. washwashed with water and saturated brine
11. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
12. filtrationThe insoluble material was filtered off
13. concentrationthe solution was concentrated under reduced pressure

ORD record

ord-d02ee8b4b9cc4d9b9d48e19d0c2ec4c4

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2