Reaktion #73016

Reaktionsgleichung

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

Ausbeute 38.0%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe resulting product was treated
2. 2
   SonstigeAfter the solvent was removed
3. 3
   Sonstigeto yield an oil
4. 4
   Temperaturthe solution was heated
5. 5
   Temperaturat reflux for 6 h
6. 6
   SonstigeThe volatiles were removed under reduced pressure
7. 7
   Sonstigethe resulting brown oil was partitioned between dichloromethane (500 mL) and water
8. 8
   TrocknenThe organic layer was dried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    Sonstigeto yield a brown oil
12. 12
    SonstigePurification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Vorschrift

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%).

Quelle