Reaktion #9492

Reaktionsgleichung

1-[3-(7-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one

3-Methoxypropionyl chloride

triethylamine

→

1-{3-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   SonstigeThe crude product obtained in Part D
3. 3
   Sonstigewas purified by flash chromatography on silica gel (
4. 4
   Wascheneluting sequentially with 100:0 and 92.5:7.5 chloroform
5. 5
   Sonstigemethanol) followed by recrystallization from acetonitrile
6. 6
   WaschenThe crystals were washed with acetonitrile and diethyl ether
7. 7
   Sonstigedried in a vacuum oven at 60° C.

Vorschrift

1-[3-(7-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one was treated according to the methods described in Parts B, C, and D of Examples 152–156. 3-Methoxypropionyl chloride was used in Part C, and triethylamine (1.3 equivalents) was added to the reaction mixture. The crude product obtained in Part D was purified by flash chromatography on silica gel (eluting sequentially with 100:0 and 92.5:7.5 chloroform:methanol) followed by recrystallization from acetonitrile. The crystals were washed with acetonitrile and diethyl ether and dried in a vacuum oven at 60° C. to provide 1-{3-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as a light grey solid.

Quelle