Valeryl chloride → HCID 57455389, compound

Valeryl chloride (1.8 mL, 15.3 mmol, 1.1 eq) was added dropwise to a solution of ethyl 4-[(3-amino[1,5]naphthyridin-4-yl)amino]butyrate (3.8 g, 13.9 mmol, 1 eq) in dichloromethane (55 mL) and stirred for one hour. The reaction mixture was concentrated under reduced pressure and was dissolved in pyridine (55 mL). Pyridine hydrochloride (0.16 g, 1.39 mmol, 0.1 eq) was added and the reaction mixture was heated to reflux for 18 hours. The reaction mixture was concentrated under reduced pressure and diluted with dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (75 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (2×30 mL). The combined organics were dried over magnesium sulfate, stirred over decolorizing charcoal, filtered through CELITE filter aid, concentrated under reduced pressure, and dried at 35° C. under high vacuum to afford 4.18 g of ethyl 4-(2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyrate as a brown solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionwas dissolved in pyridine (55 mL)
3. temperaturethe reaction mixture was heated
4. temperatureto reflux for 18 hours
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. additiondiluted with dichloromethane (100 mL) and saturated aqueous sodium bicarbonate (75 mL)
7. customThe phases were separated
8. extractionthe aqueous phase was extracted with dichloromethane (2×30 mL)
9. dry with materialThe combined organics were dried over magnesium sulfate
10. stirringstirred
11. filtrationfiltered through CELITE
12. filtrationfilter aid
13. concentrationconcentrated under reduced pressure
14. customdried at 35° C. under high vacuum

ORD record

ord-43bb95a7806042d08e46a8bc309a4412

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778963B2