Reacción #9602

Ecuación de reacción

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

Rendimiento 49.9%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed sequentially with water (50 mL) and 1% aqueous sodium carbonate (100 mL)
2. 2
   Secadodried over sodium sulfate
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroThe residue was triturated with isopropanol
5. 5
   Otrowater (10 mL/g and 1.7 mL/g) and isolated by filtration
6. 6
   ConcentraciónThe filtrate was concentrated under reduced pressure
7. 7
   Otrorecrystallized from isopropanol (5 mL/g)
8. 8
   Otrodried overnight in a vacuum oven

Procedimiento

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.

Fuente