[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([O:12][CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]2[N:1]=[C:18]([C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]([F:14])([F:24])[F:25])[NH:11][C:10]=2[CH:9]=1A mixture of 2,3-diamino-5-methoxybenzoic acid 86 (1.1 equiv) and 2-(trifluoromethyl)benzaldehyde 74 (1 equiv) and sodium metabisulfite (3 equiv) in DMF was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was diluted with water. The resulting solids were collected by filtration and dried to afford 6-methoxy-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 87 as dark yellow solid (40%).
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