反应详情

To a solution of 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopentanol (approximately 28.8 mmol, prepared as described above) in dichloromethane (200 mL) at 0° C. was added triethylamine (4.41 mL, 31.6 mmol) and ethoxyacetyl chloride (88%, 3.96 g, 30.2 mmol). After 3 h at rt, the solution was concentrated and ethanol (260 mL) and triethylamine (14 mL) were added. The resulting solution was heated at reflux for 18 h and then concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine twice and dried over MgSO4, filtered, and concentrated to 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 pure 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol (4.55 g, 49% for three steps).

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 h
5. concentrationconcentrated in vacuo
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 to an oil that
11. customformed a white solid when acetonitrile
12. additionwas added
13. customThe mixture was sonicated briefly
14. filtrationfiltered
15. customThe white powder was dried under vacuum