[CH3:1][NH:2][C:3]1[N:8]2[C:9](=[O:12])[NH:10][N:11]=[C:7]2[C:6]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:4]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([C:46]([F:49])([F:48])[F:47])=[N:44][CH:45]=1>CCOC(C)=O>[CH3:1][NH:2][C:3]1[N:8]2[C:9](=[O:12])[N:10]([CH2:39][C:40]3[CH:45]=[N:44][C:43]([C:46]([F:49])([F:47])[F:48])=[CH:42][CH:41]=3)[N:11]=[C:7]2[C:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:4]=1To a mixture of crude 5-(methylamino)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one, DMF (0.5 mL), and potassium carbonate (38 mg, 0.28 mmol) was added 5-chloromethyl-2-(trifluoromethyl)pyridine (18 mg, 0.09 mmol). The resulting reaction mixture was stirred at 70° C. for 1 h. The reaction mixture was then diluted with EtOAc, washed with water and saturated aqueous NaCl, dried (Na2SO4), and concentrated at reduced pressure. The residue was purified by preparative reverse phase HPLC to obtain 25 mg (51% over two steps) of the title compound as a light yellow solid. HPLC/MS: retention time=4.40 min, [M+H]30 =545.
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