反应详情

To a solution of 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopentanol (approximately 28.8 mmol) in dichloromethane (200 mL) at 0° C. was added triethylamine (4.41 mL, 31.6 mmol) and ethoxyacetyl chloride (88% purity, 3.96 g, 30.2 mmol). After 3 hours at room temperature, the solution was concentrated and ethanol (260 mL) and triethylamine (14 mL) were added. The resulting solution was heated at reflux for 18 hours and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine twice, dried over MgSO4, filtered, and concentrated to yield an oil that formed a white solid when acetonitrile was added. The mixture was sonicated briefly and filtered. The white powder was dried under vacuum to provide 4.55 g of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol.

1. concentrationthe solution was concentrated
2. additionethanol (260 mL) and triethylamine (14 mL) were added
3. temperatureThe resulting solution was heated
4. temperatureat reflux for 18 hours
5. concentrationconcentrated under reduced pressure
6. customThe residue was partitioned between dichloromethane and water
7. washThe organic layer was washed with brine twice
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto yield an oil that
12. additionwas added
13. customThe mixture was sonicated briefly
14. filtrationfiltered
15. customThe white powder was dried under vacuum