ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[C:23]([O:34][CH3:35])[CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[CH3:38][O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1.CS(C)=O>C(#N)C>[CH3:38][O:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH:45][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH3:33])=[C:23]([O:34][CH3:35])[CH:22]=4)=[O:20])[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13]3)=[CH:7][CH:6]=2)=[O:4])=[CH:42][CH:41]=1In a glass tube was weighed 2,2,2-trichloro-1-{10-[(2-methoxy-2′-methyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 35 (0.32 mmol), acetonitrile (2.5 mL), 4-methoxybenzylamine (0.66 mmol), and dimethylsulfoxide (1.11 mmol). The stirred solution was heated at 80° C. for 20 hours. The solvent was evaporated and the residue was dissolved in dichloromethane (5 mL), washed twice with water, dried over anhydrous sodium sulfate, and evaporated. Flash chromatography on silica gel using hexane/ethyl acetate/dichloromethane (3:1:1) provided 0.155 g (86%) of the title compound as a white solid, which was recrystallized from ethyl acetate/hexane, m.p. 178-179° C. MS [(+)ESI, m/z]: 570 [M+H]+Anal. Calcd for C36H33N3O4: C, 75.64; H, 5.82; N, 7.35. Found: C, 75.31; H, 5.83; N, 7.27.
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