Reacción #73016

Ecuación de reacción

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

Rendimiento 38.0%

Disolventes

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONthe resulting product was treated
2. 2
   OtroAfter the solvent was removed
3. 3
   Otroto yield an oil
4. 4
   Temperaturathe solution was heated
5. 5
   Temperaturaat reflux for 6 h
6. 6
   OtroThe volatiles were removed under reduced pressure
7. 7
   Otrothe resulting brown oil was partitioned between dichloromethane (500 mL) and water
8. 8
   SecadoThe organic layer was dried over Na2SO4
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    Otroto yield a brown oil
12. 12
    OtroPurification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Procedimiento

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%).

Fuente