[Cl:1][C:2]1[C:3]([CH3:15])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29]OC.CCOC(C)=O.O>CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29][NH:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([CH3:15])=[N:4]2)=[CH:9][CH:10]=1The 4-(4-Chloro-3,5-dimethyl-pyrazol-1-yl)-phenylamine (130 mg, 0.58 mmol) and 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (120 mg, 0.43 mmol) is heated in N,N-dimethylformamide (10 mL) at 100° C. for 4 h. EtOAc (100 mL) and H2O (20 mL) is then added. The EtOAc layer is washed with H2O (3×20 mL) and brine (15 mL) and dried over MgSO4. Upon removal of EtOAc, precipitate formed and the precipitate is collected and washed with MeOH and Et2O and dried to provide the title compound (64 mg, 32%). 1H NMR (400 MHz, DMSO) δ 12.56(1H, d, J=12.4 Hz), 11.46 (1H, s), 8.98 (1H, d, J=12.4 Hz), 8.50 (1H, s), 7.43-7.94 (6H, m), 2.30 (3H, s), 2.21 (3H, s); MP: 290-291° C.; Anal. Cacl. for C21H16BrClN4O2: C, 53.47; H, 3.42; N, 11.88. Found: C, 51.49; H, 2.94; N, 11.31.
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