Water → HCID 66619826, compound

Participants

Reaction Steps

A solution of tert-butyl (10S)-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate 5-oxide (1.22 g, 3.58 mmol) in 50 mL of CH2Cl2 was treated with 5 mL of concentrated aqueous ammonium hydroxide and stirred vigorously. p-Toluenesulfonyl chloride (0.68 g, 3.58 mmol) was added in one portion and the reaction became slightly exothermic. The following day the reaction was treated with 5 mL of H2O, and the layers were separated. The organic layer was washed with saturated NaHCO3 solution (2×), then brine. It was dried over Na2SO4, filtered and concentrated to give a crude solid. Chromatography (SiO2, 0-20% CMA/CHCl3) afforded an off white solid, which was recrystallized from ethyl acetate to give tert-butyl (10S)-6-amino-10-methyl-9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c]quinoline-8-carboxylate (0.26 g) as a white solid.

Provenance & Evidence