반응 #9608

반응 방정식

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

수율 64.2%

용매

chloroform

반응 조건

후처리

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
   기타The crude product was recrystallized from isopropanol (13 mL/g)
5. 5
   기타isolated by filtration
6. 6
   기타dried overnight on the filter funnel

실험 절차

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.

출처