Reacción #2079782

Ecuación de reacción

Acetic acid

sodium cyanoborohydride

acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime

tetrahydrofuran

→

1-{3-[(isopropylamino)oxy]propyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Rendimiento 86.8%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas concentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with water (100 mL)
3. 3
   ExtracciónThe mixture was extracted with chloroform (2×100 mL)
4. 4
   Secadodried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

Acetic acid (10 mL) followed by 1 M sodium cyanoborohydride in tetrahydrofuran (11.05 mL, 11.05 mmol) was added to a stirred solution of acetone O-[3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]oxime (1.50 g, 4.42 mmol) in methanol (10 mL). The reaction was stirred overnight at room temperature and then was concentrated under reduced pressure. The residue was diluted with water (100 mL) and the pH was adjusted with solid sodium hydroxide to pH 6. The mixture was extracted with chloroform (2×100 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 1.31 g of 1-{3-[(isopropylamino)oxy]propyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine.

Fuente