Water → [4-amino-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate

Participants

Reaction Steps

[1-(2-Fluoro-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate (1.67 g, 5.03 mmol) was dissolved in 50 mL of CH2Cl2 and treated with 5 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (1.05 g, 5.53 mmol) was carefully added. Rapid stirring was continued for 1 hour. The reaction mixture was then treated with 20 mL of H2O. The layers were separated and the organic portion was washed successively with 5% Na2CO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered, and concentrated under reduced pressure. Chromatography (SiO2, 2.5% methanol/CHCl3) gave 1.13 g of [4-amino-1-(2-fluoro-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methyl acetate as a light-yellow solid.

Provenance & Evidence