m-Chloroperbenzoic acid → 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

Temperature

0 °C

A solution of 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinoline (2.6 g, 8.2 mmol) in dichloromethane (100 mL) was cooled to approximately 0° C., and 3-chloroperoxybenzoic acid (3.6 g of approximately 77% pure material, 16 mmol) was added over a period of several minutes. The reaction was stirred for ten minutes at 0° C., stirred for 90 minutes at room temperature, washed with saturated aqueous sodium bicarbonate (2×35 mL, containing 1 mL of 25% w/w aqueous sodium hydroxide), dried over potassium carbonate, and filtered. The resulting solution was cooled to 0° C., and trichloroacetyl isocyanate (1.22 mL, 10.3 mmol) was added with stirring. The reaction was stirred for 15 minutes at 0° C., stirred for 75 minutes at room temperature, and concentrated under reduced pressure. The residue was dissolved in methanol (60 mL), and sodium methoxide (6.3 mL of a 25% w/w solution in methanol, 29 mmol) was added with stirring. The mixture was stirred at room temperature overnight. A precipitate formed, and the reaction mixture was cooled to approximately 0° C. The precipitate was collected by filtration, recrystallized from methanol/water, and dried overnight in a vacuum oven at 70° C. to provide 1.11 g of 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as white crystals, mp 164-166° C.

1. stirringstirred for 90 minutes at room temperature
2. washwashed with saturated aqueous sodium bicarbonate (2×35 mL, containing 1 mL of 25% w/w aqueous sodium hydroxide)
3. dry with materialdried over potassium carbonate
4. filtrationfiltered
5. temperatureThe resulting solution was cooled to 0° C.
6. stirringwith stirring
7. stirringThe reaction was stirred for 15 minutes at 0° C.
8. stirringstirred for 75 minutes at room temperature
9. concentrationconcentrated under reduced pressure
10. dissolutionThe residue was dissolved in methanol (60 mL)
11. additionsodium methoxide (6.3 mL of a 25% w/w solution in methanol, 29 mmol) was added
12. stirringwith stirring
13. stirringThe mixture was stirred at room temperature overnight
14. customA precipitate formed
15. temperaturethe reaction mixture was cooled to approximately 0° C
16. filtrationThe precipitate was collected by filtration
17. customrecrystallized from methanol/water
18. customdried overnight in a vacuum oven at 70° C.

ORD record

ord-8e73b2786fa3481488585593c9916879

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579359B2