[Cl:1][C:2]1[C:3]([O:13][CH:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:15]([F:18])([F:17])[F:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8](N)=[CH:7][CH:6]=2.N([O-])=O.[Na+].NC(N)=O.[I-:33].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>Cl.O>[Cl:1][C:2]1[C:3]([O:13][CH:14]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:15]([F:18])([F:17])[F:16])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([I:33])=[CH:7][CH:6]=2In 2.0 mol/L hydrochloric acid (50.0 mL) was dissolved 3-chloro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline-6-amine (2.00 g, 5.64 mmol) obtained in Step 3 and the mixture was cooled to 0° C. Sodium nitrite (506 mg, 7.33 mmol) was added and the mixture was stirred at 0° C. for 10 minutes. Urea (508 mg, 8.46 mmol) was added to the reaction mixture and the mixture was stirred at 0° C. for 10 minutes. Potassium iodide (2.34 g, 14.1 mmol) dissolved in water (10.0 mL) was slowly added and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2) to give Compound A47 (868 mg, 33% yield).
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