FC(F)(F)C(O)=O.[NH2:8][CH2:9][C:10]1[C:11]([F:29])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:23]=[C:24]([CH:26]([F:28])[F:27])[CH:25]=2)[C:21]#[N:22])[C:13]([Cl:16])=[CH:14][CH:15]=1.[Br:30][C:31]1[N:32]=[CH:33][NH:34][C:35]=1[C:36](O)=[O:37].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:30][C:31]1[N:32]=[CH:33][NH:34][C:35]=1[C:36]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][C:18]2[CH:25]=[C:24]([CH:26]([F:28])[F:27])[CH:23]=[C:20]([C:21]#[N:22])[CH:19]=2)[C:11]=1[F:29])=[O:37]To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(difluoromethyl)benzonitrile trifluoroacetate (90 mg, 0.204 mmol), 4-bromo-1H-imidazole-5-carboxylic acid (39.0 mg, 0.204 mmol) and HOBT (31.3 mg, 0.204 mmol) in DMF (3 ml) was added EDC (39.1 mg, 0.204 mmol) and the reaction mixture was stirred at RT for 30 minutes. The crude material was purified via reverse phase HPLC to give the title compound (56 mg, 55% yield). 1H NMR (DMSO-d6) δ ppm 8.42 (br. s., 1H) 7.85 (s, 1H) 7.79 (s, 1H) 7.72 (s, 1H) 7.47-7.58 (m, 2H) 7.38 (t, 1H) 7.07 (t, 1H) 4.51 (d, 2H). LC-MS (ES+) m/z 499.00 [M+H].
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