C(Cl)CCl.[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:47]([OH:49])=O)=[CH:16][C:17]=3[N:18]3[CH2:24][C:23]([C:25]4[N:29]([CH:30]5[CH2:32][CH2:31]5)[N:28]=[C:27]([CH:33]([CH3:35])[CH3:34])[C:26]=4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:22][C:21]4[CH:41]=[C:42]([O:45][CH3:46])[CH:43]=[CH:44][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:50][CH:51]([S:53]([NH2:56])(=[O:55])=[O:54])[CH3:52]>CN(C1C=CN=CC=1)C.ClC(Cl)C.CCOC(C)=O>[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:47](=[O:49])[NH:56][S:53]([CH:51]([CH3:52])[CH3:50])(=[O:55])=[O:54])=[CH:16][C:17]=3[N:18]3[CH2:24][C:23]([C:25]4[N:29]([CH:30]5[CH2:31][CH2:32]5)[N:28]=[C:27]([CH:33]([CH3:35])[CH3:34])[C:26]=4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:22][C:21]4[CH:41]=[C:42]([O:45][CH3:46])[CH:43]=[CH:44][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1EDC (151 mg, 0.790 mmol) was added to a stirring solution of 13-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (320 mg, 0.527 mmol), propane-2-sulfonamide (227 mg, 1.843 mmol), DMAP (193 mg, 1.58 mmol) in dichloroethane (5 mL) at room temperature. The reaction was allowed to stir overnight. The mixture was diluted with EtOAc and washed with 1M HCl, sat NaHCO3 and Brine. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product (375 mg, 0.526 mmol, quant) as a light brown residue consistent by LCMS.
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