تفاعل #73006

معادلة التفاعل

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

المردود 53.0%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. for 1 h
2. 2
   ترشيحwas filtered
3. 3
   workup.ADDITIONThe filtrate was diluted with dichloromethane (30 mL) and saturated aqueous sodium bicarbonate (30 mL)
4. 4
   أخرىThe layers were separated
5. 5
   استخلاصthe aqueous layer was extracted with dichloromethane (20 mL)
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىto afford an orange solid, which
10. 10
    أخرىwas purified by HPFC (silica gel, eluted with 0-35% CMA/chloroform)
11. 11
    تركيزThe appropriate fractions were concentrated
12. 12
    أخرىto afford a tan solid
13. 13
    أخرىthat was crystallized from chloroform/hexanes
14. 14
    أخرىdried at 75° C. under vacuum

الإجراء التجريبي

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.

المصدر