Reaktion #72972

Reaktionsgleichung

1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopentanol

triethylamine

ethoxyacetyl chloride

→

1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol

Ausbeute 49.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe solution was concentrated
2. 2
   workup.ADDITIONethanol (260 mL) and triethylamine (14 mL) were added
3. 3
   TemperaturThe resulting solution was heated
4. 4
   Temperaturat reflux for 18 h
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was partitioned between dichloromethane and water
7. 7
   WaschenThe organic layer was washed with brine twice
8. 8
   Trocknendried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated to an oil that
11. 11
    Sonstigeformed a white solid when acetonitrile
12. 12
    workup.ADDITIONwas added
13. 13
    SonstigeThe mixture was sonicated briefly
14. 14
    Filtrationfiltered
15. 15
    SonstigeThe white powder was dried under vacuum

Vorschrift

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).

Quelle