[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([OH:19])=O)=[CH:4][CH:3]=1.[NH:20]1[C:28]2[C:23](=[CH:24][C:25]([NH2:29])=[CH:26][CH:27]=2)[CH:22]=[N:21]1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[N:11]([CH3:15])[C:10]([CH3:16])=[C:9]2[C:17]([NH:29][C:25]2[CH:24]=[C:23]3[C:28](=[CH:27][CH:26]=2)[NH:20][N:21]=[CH:22]3)=[O:19])=[CH:6][CH:7]=1The product of step 2 (335 mg, 1.20 mmol, 1.00 equiv), 1H-indazol-5-amine (191 mg, 1.44 mmol, 1.20 equiv) and EDC (276 mg, 1.44 mmol, 1.20 equiv) were suspended in 10.0 mL DMF. Et3N (0.191 mL, 1.44 mmol, 1.20 equiv) was added and the solution was stirred 5 days at room temperature. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (40% 100% EtOAc) to provide 0.060 g (13%) of the title compound as a white solid. MS (ES+) m/e 395 [M+H]+
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