Reaktion #9608

Reaktionsgleichung

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

Ausbeute 64.2%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

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
   SonstigeThe crude product was recrystallized from isopropanol (13 mL/g)
5. 5
   Sonstigeisolated by filtration
6. 6
   Sonstigedried overnight on the filter funnel

Vorschrift

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.

Quelle