C[O-].[Na+].C(=O)(O)O.[NH2:8][NH:9][C:10]([NH2:12])=[NH:11].[F:13][C:14]([F:26])([F:25])[C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18](OC)=O>CO>[F:13][C:14]([F:25])([F:26])[C:15]1[CH:16]=[C:17]([C:18]2[NH:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH:22]=[CH:23][CH:24]=1To a solution of sodium methanolate (1.05 g, 19.44 mmol, 4.00 equiv) in methanol (40 mL) at 0° C. was added aminoguanidine bicarbonate (2.66 g, 19.54 mmol, 4.00 equiv) in several batches. To this was added dropwise a solution of methyl 3-(trifluoromethyl)benzoate (1 g, 4.90 mmol, 1.00 equiv) in methanol (10 mL) with stirring at 0° C. The resulting solution was then stirred overnight at 75° C. in an oil bath. The reaction was then quenched with 10 mL of water/ice, the solution adjusted to pH 3-4 with hydrochloric acid (1 mol/L), and the solids were collected by filtration To afford 150 mg (13%) of 5-(3-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-amine as a yellow solid.
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