Réaction #9608

Équation de réaction

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

Rendement 64.2%

Solvants

chloroform

Conditions de réaction

Traitement

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
   AutreThe crude product was recrystallized from isopropanol (13 mL/g)
5. 5
   Autreisolated by filtration
6. 6
   Autredried overnight on the filter funnel

Mode opératoire

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.

Source