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N-Methylacetamide (0.087 mL, 1.14 mmol) and 2,6-lutidine (0.266 mL, 2.28 mL) were dissolved in dichloromethane (5.7 mL), and the mixture was stirred for 40 minutes after adding oxalyl chloride (0.100 mL, 1.14 mL) at 0° C. The mixture was stirred for 5 hours after adding 3-iodobenzohydrazide (300 mg, 1.14 mmol) obtained in Step 1 of Example 52, and then at 100° C. for 3 hours after adding a saturated aqueous sodium bicarbonate solution (5.7 mL). After cooling, water and chloroform were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 3-(3-iodophenyl)-4,5-dimethyl-1,2,4-triazole as a crude purified product (250 mg). The resulting crude purified product (250 mg) of 3-(3-iodophenyl)-4,5-dimethyl-1,2,4-triazole, (S)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (376 mg, 1.50 mmol)) obtained in Reference Example 3, copper iodide(I) (142 mg, 0.750 mmol), and tripotassium phosphate (532 mg, 2.51 mmol) were dissolved in 1,4-dioxane (4.6 mL), and the mixture was stirred at 100° C. for 10 hours after adding ethylenediamine (0.10 mL, 1.50 mmol). Insolubles were filtered through sellite, and the residue was washed with chloroform. The filtrate was collected, and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give (S)-5-[3-(4,5-dimethyl-1,2,4-triazol-3-yl)phenyl]-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (74.2 mg, 15%).

1. stirringThe mixture was stirred for 5 hours
2. temperatureAfter cooling
3. customto separate the organic layer
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe resulting residue was then purified by silica gel column chromatography