Hydrochloric Acid → 7-(3,5-dimethyl-4-isoxazolyl)-N4-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3,4-quinolinediamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3-nitro-4-quinolinamine (for a preparation see intermediate 69, 1.13 g) in ethanol was added hydrochloric acid (2 ml, conc). Tin (II) chloride dihydrate (2.32 g) was added and the mixture was stirred at 40° C. for 1 h. The reaction mixture was cooled, diluted with water and basified using sodium hydroxide solution (1N). The formed precipitate was filtered through Celite and rinsed with DCM. The filtrate was washed with water and the organic was dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with DCM/methanol (98:2 then 93:7) to give 7-(3,5-dimethyl-4-isoxazolyl)-N4-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-(methyloxy)-3,4-quinolinediamine (0.6 g) as a beige foam.

Provenance & Evidence