تفاعل #1451249

معادلة التفاعل

potassium tert-butoxide

tert-butyl 3-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate

potassium tert-butoxide

→

tert-butyl 3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate

المردود 51.1%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction was stirred overnight at ambient temperature
2. 2
   تركيزconcentrated under reduced pressure
3. 3
   أخرىThe crude reaction mixture
4. 4
   أخرىwas purified by column chromatography on silica gel (
5. 5
   غسيلeluting with 2 N ammonia in methanol/chloroform in a 67-minute gradient from 0:100 to 3:97) and
6. 6
   أخرىrecrystallized sequentially from dichloromethane and acetonitrile

الإجراء التجريبي

Under a nitrogen atmosphere, potassium tert-butoxide (142.7 mL of a 1 M solution in THF) was added to a solution of tert-butyl 3-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (57.2 g, 118.9 mmol) in THF (142.7 mL). After the reaction was stirred at ambient temperature for ten minutes, additional potassium tert-butoxide (32 mL of a 1 M solution in THF) was added. The reaction was stirred overnight at ambient temperature and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 67-minute gradient from 0:100 to 3:97) and recrystallized sequentially from dichloromethane and acetonitrile to provide 26.99 g of tert-butyl 3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

المصدر