Ethyl isothiocyanatoformate → ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}-5-methylphenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate

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To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]-5-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (2.23 g, 5.43 mmol) in DMSO (30 mL) was added ethyl isothiocyanatoformate (770 μL, 6.52 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→50/50) to give the title compound (2.65 g, 88%) as a pale-yellow oil.

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