[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:15]=[C:14]([Cl:16])[C:11]([C:12]#[N:13])=[C:10]([Cl:17])[CH:9]=2)[N:3]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.C(O)(=O)C.Cl>CO>[Cl:17][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[N:3]=[C:2]([NH:1][CH2:24][C:23]3[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:28])[F:29])=[CH:27][CH:26]=3)[NH:6][N:5]=2)[CH:15]=[C:14]([Cl:16])[C:11]=1[C:12]#[N:13]To a solution of 4-(5-Amino-1H-[1,2,4]triazol-3-ylamino)-2,6-dichloro-benzonitrile (60 mg, 223 μmol) in MeOH (3.5 ml) was added 4-(trifluoromethyl)benzaldehyde (46.6 mg, 268 μmol, Aldrich) followed by acetic acid (36.7 mg, 35 μl, 611 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (32.2 mg, 349 μmol) was added and the stirring was continued for 4 days. The reaction mixture was poured into 0.1N HCl solution (20 ml) and extracted with EtOAc (3×20 ml). The combined organic solution was washed with brine, dried and concentrated in vacuo. Crystallization from DCM afforded a white solid as desired product (55 mg, 57% yield). MS +m/z: 427 (M+H)+
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