Thionyl chloride was added at −20° C. to a solution of 1-(benzyloxycarbonyl)cyclopropanecarboxylic acid (97.98 g) in tetrahydrofuran (200 ml) and N-methylpyrrolidone (200 ml) and stirred for 30 minutes. A solution of 4-(4-amino-3-fluorophenoxy)pyridine-2-carboxyamide (100 g) and N-methylmorpholine (40.91 g) in N-methylpyrrolidone (600 ml) were added to the reaction mixture at the same temperature and stirred for 1 hour at 10° C. Water (100 g) was added to the reaction mixture and stirred for 1 hour at 20° C. After confirming the crystal precipitation, a 1N sodium hydroxide aqueous solution (1 L) was added and further stirred for 19 hours. The precipitated solid was collected by filtration and washed with water (500 g). The obtained solid was dried for 20 hours at 60° C. to give 176.7 g of the title compound.
