Water → HCID 23653550, compound

Participants

Reaction Steps

A solution of (11S)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (85 mg, 0.316 mmol) in 5 mL of CH2Cl2 was treated with 1 mL of concentrated aqueous ammonium hydroxide and stirred vigorously. p-Toluenesulfonyl chloride (60 mg, 0.316 mmol) was added in one portion. The following day the reaction was treated with 5 mL of H2O and 10 mL of CH2Cl2, and the layers were separated. The organic layer was washed sequentially with saturated NaHCO3 solution (2×) and brine, dried over Na2SO4, filtered, and concentrated to give a light yellow solid. Chromatography (AFC, SiO2, 0-20% CMA/CHCl3) afforded (11s)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (25 mg) as a white solid, m.p. 218-223° C.

Provenance & Evidence