Water → (11S)-11-{[(4-fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Participants

Reaction Steps

(11S)-11-{[(4-Fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (732 mg, 1.93 mmol) was dissolved in 50 mL of CH2Cl2 and treated with 5 mL of concentrated NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (370 mg, 1.93 mmol) was carefully added. Rapid stirring continued overnight. The reaction mixture was treated with 5 mL of H2O, and the layers were separated. The organic portion was washed with saturated NaHCO3 (2×50 mL) followed by brine (50 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated under reduced pressure to give a crude orange solid. Chromatography (SiO2, 10-30% CMA/CHCl3) gave 236 mg of (11S)-11-{[(4-fluorobenzyl)oxy]methyl}-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid, mp 134-137° C.

Provenance & Evidence