Reaktion #73006

Reaktionsgleichung

p-toluenesulfonyl chloride

ammonium hydroxide

1-{3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}cyclohexanol

m-CPBA

→

1-{3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}cyclohexanol

Ausbeute 53.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. for 1 h
2. 2
   Filtrationwas filtered
3. 3
   workup.ADDITIONThe filtrate was diluted with dichloromethane (30 mL) and saturated aqueous sodium bicarbonate (30 mL)
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous layer was extracted with dichloromethane (20 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto afford an orange solid, which
10. 10
    Sonstigewas purified by HPFC (silica gel, eluted with 0-35% CMA/chloroform)
11. 11
    EinengenThe appropriate fractions were concentrated
12. 12
    Sonstigeto afford a tan solid
13. 13
    Sonstigethat was crystallized from chloroform/hexanes
14. 14
    Sonstigedried at 75° C. under vacuum

Vorschrift

To a solution of 1-{3-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}cyclohexanol (1.10 g, 2.99 mmol) in chloroform (15 mL) at rt was added m-CPBA (0.96 g, 3.89 mmol) in portions. The reaction was stirred for 1.5 h, then was cooled to 0° C. and concentrated ammonium hydroxide (5 mL) was added followed by portionwise addition of p-toluenesulfonyl chloride (0.630 g, 3.29 mmol). The mixture was stirred at 0° C. for 1 h, then was filtered. The filtrate was diluted with dichloromethane (30 mL) and saturated aqueous sodium bicarbonate (30 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (20 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated to afford an orange solid, which was purified by HPFC (silica gel, eluted with 0-35% CMA/chloroform). The appropriate fractions were concentrated to afford a tan solid that was crystallized from chloroform/hexanes and dried at 75° C. under vacuum to afford 1-{3-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}cyclohexanol as white crystals (600 mg, 53%), mp 175-176° C. Anal. calcd for C22H30N4O2: C, 69.08; H, 7.91; N, 14.65.

Quelle