Reaktion #9479

Reaktionsgleichung

1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

3-methoxypropionyl chloride

→

1-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

Ausbeute 37.6%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude product was recrystallized from 2:1 ethyl acetate
2. 2
   Sonstigehexane and then purified by flash column chromatography on silica gel (
3. 3
   Wascheneluting sequentially with 60:40 acetone

Vorschrift

The method described in Part A of Example 9 was used to react 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (29.0 g, 93.5 mmol) with 3-methoxypropionyl chloride (11.5 g, 93.5 mmol). The crude product was recrystallized from 2:1 ethyl acetate:hexane and then purified by flash column chromatography on silica gel (eluting sequentially with 60:40 acetone:toluene and acetone). The resulting solid was recystallized from 3:1 ethyl acetate hexane to provide 13.3 g of 1-[7-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as translucent crystals.

Quelle