Potassium Carbonate → tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate

Temperature

50 °C

To a solution of the hydrochloride salt of tert-butyl 2-({2-chloro-3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)ethylcarbamate (2.50 g, 5.44 mmol) in 9:1 ethanol/water (50 mL) was added a solution of potassium carbonate (1.12 g, 8.16 mmol) in water (5 mL). The solution was heated to 50° C. for five hours. The solution was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to a pale yellow solid that was purified by flash chromatography (silica gel, gradient elution from 1:1 to 4:1 ethyl acetate/hexane) to afford the tert-butyl 2-(4-chloro-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate as a white solid (1.55 g).

1. concentrationThe solution was concentrated under reduced pressure
2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane
3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
4. washThe combined organic layers were washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated to a pale yellow solid
8. customthat was purified by flash chromatography (silica gel, gradient elution from 1:1 to 4:1 ethyl acetate/hexane)

ORD record

ord-a73e6fa97d734a05b5be0a872b0c677a

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915281B2