反应详情

Triethylamine (2.67 mL, 5 eq) was added to a chilled (ice/water bath) suspension of N-{2-[4-amino-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide (1.5 g, 1 eq) in dichloromethane (150 mL). A solution of butyl chloroformate (1.73 g, 3.3 eq) in dichloromethane (5 mL) was added dropwise to give a clear solution. The reaction mixture was allowed to come to ambient temperature with stirring for 24 hours. The reaction mixture was washed sequentially with water (150 mL), 4% sodium carbonate (150 mL), water (150 mL), and brine (150 mL). The organic layer was concentrated under reduced pressure. The residue was purified by automated flash chromatography (silica gel eluted with a linear gradient of 0-20% CMA in chloroform, 1500 mL) followed by recrystallization from diethyl ether to provide 1.23 g of propyl 2-ethoxymethyl-1-{2-methyl-2-[(methylsulfonyl)amino]propyl}-1H-imidazo[4,5-c]quinolin-4-ylcarbamate as a white powder, mp 125-127° C. Anal calcd for C23H33N5O5S: C, 56.19; H, 6.77; N, 14.25. Found: C, 56.35; H, 6.65; N, 14.24.

1. temperaturea chilled
2. customto give a clear solution
3. customto come to ambient temperature
4. washThe reaction mixture was washed sequentially with water (150 mL), 4% sodium carbonate (150 mL), water (150 mL), and brine (150 mL)
5. concentrationThe organic layer was concentrated under reduced pressure
6. customThe residue was purified by automated flash chromatography (silica gel
7. washeluted with a linear gradient of 0-20% CMA in chloroform
8. custom1500 mL) followed by recrystallization from diethyl ether