Thionyl Chloride → HCID 67041486, compound

Participants

Reaction Steps

The methods described in Examples 30 and 31 were repeated on a larger scale to provide (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-2-yl)methanol. The reaction described in Example 31 was heated at reflux and was complete within three hours. Thionyl chloride (0.45 mL, 6.17 mmol) was added dropwise to a suspension of (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-2-yl)methanol (1.2 g, 3.08 mmol) in dichloromethane (30 mL), and the mixture was stirred at room temperature for 1.8 hours. The volatiles were removed under reduced pressure, and the residue was combined with material from another run, triturated with a mixture of ethanol and diethyl ether, and isolated by filtration to provide 1.54 g 2-(chloromethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride.

Provenance & Evidence