Hydrochloric Acid → HCID 58869099, compound

Participants

Reaction Steps

To a solution of N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxy-N′-(trimethylsilyl)urea (4.1 g, 9.9 mmol) in tetrahydrofuran (75 mL) was added 10% aqueous HCl (5 mL). The reaction mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure and the residue was neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted with 10% methanol/dichloromethane solution. The organic layer was concentrated under reduced pressure and the crude product was recrystallized twice from methanol. The crystals were dissolved in hot methanol, filtered through a micron filter, and concentrated under reduced pressure to afford a solid that was crystallized from 5% methanol in dichloromethane to yield 0.264 g of N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N-methoxyurea as a yellow powder, mp 158-160° C.

Provenance & Evidence