Pyridine → 3-methoxy-2,2-dimethylpropionic acid 5-[(R)-[3-(2-acetoxyethoxy)-2-fluoro-5-methoxyphenyl]-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)methyl]-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester

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Under nitrogen atmosphere, a mixture of [1-amino(4-{[(R)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl](5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]-triazol-3-yl)methyl]amino}phenyl)methylene]carbamic acid 2-methylallyl ester (1.0 g, 1.69 mmol), 3-methoxy-2,2-dimethylpropionic acid chloromethyl ester (641 mg, 3.55 mmol), rubidium carbonate (312 mg, 1.35 mmol), and N,N-dimethylacetamide (30 mL) was stirred at 85° C. for 115 minutes. After cooling to room temperature, pyridine (0.69 mL, 8.45 mmol), 4-dimethylaminopyridine (20.7 mg, 0.169 mmol), and acetic anhydride (0.32 mL, 3.39 mmol) were added to the reaction solution, and the resulting mixture was stirred at room temperature for 2 hours. Ethyl acetate (150 mL) and water (150 mL) were added to the reaction mixture, and the resulting mixture was extracted. The organic layer was collected, sequentially washed with water (100 mL) and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of ethyl acetate-methanol) to obtain the captioned compound (610 mg) as a solid.

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