Réaction #9602

Équation de réaction

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

triethylamine

cyclopentanecarbonyl chloride

→

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

Rendement 49.9%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Lavagewashed sequentially with water (50 mL) and 1% aqueous sodium carbonate (100 mL)
2. 2
   Séchagedried over sodium sulfate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   AutreThe residue was triturated with isopropanol
5. 5
   Autrewater (10 mL/g and 1.7 mL/g) and isolated by filtration
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   Autrerecrystallized from isopropanol (5 mL/g)
8. 8
   Autredried overnight in a vacuum oven

Mode opératoire

A suspension of 1-(4-aminobutyl)-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.42 g, 6.4 mmol) and triethylamine (0.99 mL, 7.1 mmol) in chloroform (240 mL) was cooled to 0° C., and cyclopentanecarbonyl chloride (0.78 mL, 6.4 mmol) was added dropwise over a period of five minutes. The reaction was stirred for ten minutes, washed sequentially with water (50 mL) and 1% aqueous sodium carbonate (100 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was triturated with isopropanol:water (10 mL/g and 1.7 mL/g) and isolated by filtration. The filtrate was concentrated under reduced pressure and recrystallized from isopropanol (5 mL/g). The two solids were combined and dried overnight in a vacuum oven to provide 1.51 g of N-{4-[4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}cyclopentanecarboxamide as a light yellow solid.

Source