Sodium Hydroxide → HCID 69507359, compound

Ethoxyacetyl chloride (4.2 mL, 37.4 mmol, 1.1 eq) was added dropwise over 8 minutes to a solution of N4-(4,4-dimethoxybutyl)[1,5]naphthyridine-3,4-diamine (9.50 g, 34.0 mmol) in dichloromethane (140 mL) and stirred at ambient temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethanol (140 mL). Sodium hydroxide (6M) solution (8.5 mL, 51 mmol) was added to the reaction mixture, which was then heated for 60° C. for 3 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in dichloromethane (150 mL) and water (100 mL). The pH of the mixture was adjusted to 7 and the layers were separated. The aqueous layer was back-extracted with dichloromethane (2×50 mL) and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 10.52 g of 1-(4,4-dimethoxybutyl)-2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridine.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in ethanol (140 mL)
3. temperaturewas then heated for 60° C. for 3 hours
4. temperatureThe mixture was cooled to ambient temperature
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in dichloromethane (150 mL)
7. customthe layers were separated
8. extractionThe aqueous layer was back-extracted with dichloromethane (2×50 mL)
9. dry with materialthe combined organic layers were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure

ORD record

ord-93fe2caa310f42a68abdeb4f89862e6a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778963B2