반응 #73016

반응 방정식

Ethoxyacetyl chloride

tert-butyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexylcarbamate

Sodium hydroxide

→

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

수율 38.0%

용매

ethanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONthe resulting product was treated
2. 2
   기타After the solvent was removed
3. 3
   기타to yield an oil
4. 4
   온도the solution was heated
5. 5
   온도at reflux for 6 h
6. 6
   기타The volatiles were removed under reduced pressure
7. 7
   기타the resulting brown oil was partitioned between dichloromethane (500 mL) and water
8. 8
   건조The organic layer was dried over Na2SO4
9. 9
   여과filtered
10. 10
    농축concentrated under reduced pressure
11. 11
    기타to yield a brown oil
12. 12
    기타Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

실험 절차

Ethoxyacetyl chloride (9.00 g, 73.4 mmol) was reacted with tert-butyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexylcarbamate (27.2 g, 73.4 mmol) according to the method described in Part E of Example 9 and the resulting product was treated according to the method described in Part E of Example 9. After the solvent was removed to yield an oil, the oil was dissolved in ethanol (300 mL) and water (30 mL). Sodium hydroxide (4.3 g, 108 mmol) was added and the solution was heated at reflux for 6 h. The volatiles were removed under reduced pressure and the resulting brown oil was partitioned between dichloromethane (500 mL) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a brown oil. Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes) provided tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate as a brown solid (11.9 g, 38%).

출처