تفاعل #73016

معادلة التفاعل

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

المردود 38.0%

المذيبات

ethanol

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONthe resulting product was treated
2. 2
   أخرىAfter the solvent was removed
3. 3
   أخرىto yield an oil
4. 4
   درجة الحرارةthe solution was heated
5. 5
   درجة الحرارةat reflux for 6 h
6. 6
   أخرىThe volatiles were removed under reduced pressure
7. 7
   أخرىthe resulting brown oil was partitioned between dichloromethane (500 mL) and water
8. 8
   تجفيفThe organic layer was dried over Na2SO4
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىto yield a brown oil
12. 12
    أخرىPurification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

الإجراء التجريبي

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%).

المصدر