Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[N:15]3[C:11]([O:12][CH:13]=[CH:14]3)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])=[CH:4][CH:3]=1.C(O)CC.O.[NH2:29][NH2:30]>C(Cl)Cl>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[C:9]1[N:10]=[C:11]2[N:15]([C:8]=1[C:5]1[N:6]=[N:7][C:2]([NH:29][NH2:30])=[CH:3][CH:4]=1)[CH:14]=[CH:13][O:12]2To a flask was added 5-(6-chloropyridazin-3-yl)-6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole (4.00 g, 12.0 mmol), 1-propanol (80 mL) and hydrazine hydrate (5.89 mL, 120 mmol). The reaction mixture was heated at about 100° C. for about 20 h. The reaction mixture was cooled to ambient temperature and then diluted with DCM (100 mL). The organic layer was washed with saturated aqueous NaHCO3 (80 mL), dried with MgSO4, filtered and concentrated under reduced pressure to give the title compound (3.04 g, 77%) as a solid. LC/MS (Table 1, Method g) Rt=1.58 min; MS m/z: 329.1 (M+H)+.
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