Nitrogen → Tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate

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Reaction Steps

To a flask charged with N2 was added tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)-pyrrolo-[2,1-f][1,2,4]triazin-7-yl}-3,6-dihydropyridine-1(2H)-carboxylate (424 mg, 0.629 mmol, 1.0 eq) followed by glacial acetic acid (40 mL). To this solution was added platinum oxide (42 mg, 10% w/w). The reaction solution was evacuated via vacuum and replaced with nitrogen (5×). The reaction mixture was then evacuated again via vacuum and placed under 1 atm of hydrogen and was allowed to stir for 17 hours. The solution was filtered through a pad of celite, washed with acetic acid and concentrated. The crude concentrate was dissolved in EtOAc and washed with saturated sodium bicarbonate. The organic layer was dried (Na2SO4), filtered, condensed, and purified via flash chromatography (1:1 tetrahydrofuran/hexanes). The purified fractions were collected, evaporated, and left under vacuum overnight to yield the title compound (320 mg, 75.3% yield). 1H-NMR (DMSO-d6) MS [M+H]+=676; LCMS RT=3.52 min.

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