تفاعل #9608

معادلة التفاعل

cyclopentanecarbonyl chloride

Cyclopentanecarbonyl chloride

1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine

triethylamine

→

N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}cyclopentanecarboxamide

المردود 64.2%

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   workup.WAITstored for three days in a refrigerator
2. 2
   workup.STIRRINGthe reaction was stirred for 30 minutes
3. 3
   workup.ADDITIONtreated
4. 4
   أخرىThe crude product was recrystallized from isopropanol (13 mL/g)
5. 5
   أخرىisolated by filtration
6. 6
   أخرىdried overnight on the filter funnel

الإجراء التجريبي

Cyclopentanecarbonyl chloride (0.80 mL, 6.6 mmol) was added dropwise over a period of five minutes to a suspension of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) and triethylamine (0.78 mL, 5.6 mmol) in chloroform (200 mL). The reaction was stirred for 2.5 hours and then stored for three days in a refrigerator. Additional cyclopentanecarbonyl chloride (0.18 mL) was added, and the reaction was stirred for 30 minutes and treated as described for Examples 558–583. The crude product was recrystallized from isopropanol (13 mL/g), isolated by filtration, and dried overnight on the filter funnel to provide 1.60 g of N-{4-[4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}cyclopentanecarboxamide as a white solid.

المصدر