Reaktion #9609

Reaktionsgleichung

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

triethylamine

methanesulfonyl chloride

triethylamine

methanesulfonyl chloride

→

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

Ausbeute 37.4%

Lösungsmittel

chloroform

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature after 15 minutes
2. 2
   Sonstigethe reaction to completion
3. 3
   EinengenThe reaction was concentrated under reduced pressure
4. 4
   Sonstigethe residue was partitioned between 1% aqueous sodium carbonate and chloroform
5. 5
   workup.ADDITIONThe aqueous layer was adjusted to pH 13 with the addition of saturated aqueous sodium bicarbonate and 50% aqueous sodium hydroxide
6. 6
   SonstigeThe precipitate was isolated by filtration
7. 7
   Sonstigeair-dried
8. 8
   SonstigeThe crude product was recrystallized from isopropanol
9. 9
   Trocknenwater (15 mL/g:1.5 mL/g) and dried in a drying oven for several days

Vorschrift

A suspension of 1-(4-aminobutyl)-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.27 g, 8.7 mmol) and triethylamine (3.82 mL, 11.3 mmol) in chloroform (165 mL) was cooled to 0° C. A cold solution of methanesulfonyl chloride (1.37 mL, 9.6 mmol) in chloroform (10 mL) was slowly added. The reaction was allowed to warm to ambient temperature after 15 minutes. Additional triethylamine (3.74 mL) and methanesulfonyl chloride (2.12 mL) were added over the course of several days to drive the reaction to completion. The reaction was concentrated under reduced pressure, and the residue was partitioned between 1% aqueous sodium carbonate and chloroform. The aqueous layer was adjusted to pH 13 with the addition of saturated aqueous sodium bicarbonate and 50% aqueous sodium hydroxide. The precipitate was isolated by filtration, air-dried, and combined with material from another run. The crude product was recrystallized from isopropanol:water (15 mL/g:1.5 mL/g) and dried in a drying oven for several days to provide 1.48 g of N-{4-[4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}methanesulfonamide as a white solid.

Quelle