Pyridine → N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide

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Reaction Steps

To a cold (0° C.) mixture of pyridine (0.20 mL, 2.424 mmol), 2-amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile (starting compound 2, 1.010 g, 2.424 mmol), acetonitrile (10 mL) and THF (2 mL) was added dropwise a solution of 5-oxotetrahydro-2-furancarbonyl chloride (0.360 g, 2.424 mmol) in acetonitrile (4 mL). The mixture was stirred for 2 hrs., allowed to warm to room temperature, stirred for 1 hr., and extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica-gel (hexane:Ethyl acetate, 7:3-5:5) to give N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide as a white solid (0.982 g, yield 77%).

Provenance & Evidence