تفاعل #72972

معادلة التفاعل

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

triethylamine

ethoxyacetyl chloride

→

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

المردود 49.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   تركيزthe solution was concentrated
2. 2
   workup.ADDITIONethanol (260 mL) and triethylamine (14 mL) were added
3. 3
   درجة الحرارةThe resulting solution was heated
4. 4
   درجة الحرارةat reflux for 18 h
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was partitioned between dichloromethane and water
7. 7
   غسيلThe organic layer was washed with brine twice
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated to an oil that
11. 11
    أخرىformed a white solid when acetonitrile
12. 12
    workup.ADDITIONwas added
13. 13
    أخرىThe mixture was sonicated briefly
14. 14
    ترشيحfiltered
15. 15
    أخرىThe white powder was dried under vacuum

الإجراء التجريبي

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).

المصدر