2-Pyridinemethanamine → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine

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A solution of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-3-nitroquinoline (for a preparation see intermediate 18, 2.5 g,) and (2-pyridinylmethyl)amine (1.41 g) in acetonitrile (30 ml) were heated at 80° C. for 2 h. The mixture was extracted with DCM and the organic washed with a saturated solution of sodium hydrogen carbonate, dried over Na2SO4, filtered and concentrated to dryness. The residue was taken-up in diethyl ether, filtered and dried under vacuum. The residue was dissolved in ethanol (20 ml) and HCl (3.8 ml, conc.). Tin (II) chloride dihydrate (5.6 g) was then added in four portions and the reaction mixture was stirred for 1 h at 40° C. The mixture was hydrolysed using sodium hydroxide (1N), extracted with DCM and the organic were dried over Na2SO4. The mixture was filtered through Celite and concentrated to dryness. The crude product was purified by chromatography on silica gel eluting with DCM/methanol (56.5/3.5) to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(pyridin-2-ylmethyl)quinoline-3,4-diamine (500 mg) as a clear brown foam.

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