[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O)(=[O:4])=[O:3].CCN(C(C)C)C(C)C.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:39]1([C:45]2[C:46]3[CH:47]=[CH:48][C:49]([C:70]([O:72][CH3:73])=[O:71])=[CH:50][C:51]=3[N:52]3[C:59]=2[C:58]2[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=2[O:56][CH2:55][C@H:54]([N:64]([CH3:69])[CH2:65][CH2:66][NH:67][CH3:68])[CH2:53]3)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C=O)C>[NH2:1][S:2]([CH2:5][CH2:6][CH2:7][C:8]([N:67]([CH3:68])[CH2:66][CH2:65][N:64]([CH3:69])[C@@H:54]1[CH2:53][N:52]2[C:51]3[CH:50]=[C:49]([C:70]([O:72][CH3:73])=[O:71])[CH:48]=[CH:47][C:46]=3[C:45]([CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]3)=[C:59]2[C:58]2[CH:60]=[CH:61][CH:62]=[CH:63][C:57]=2[O:56][CH2:55]1)=[O:10])(=[O:4])=[O:3]4-(aminosulfonyl)butanoic acid (1.2 eq.), DIPEA (2 eq.), DIC (1.1 eq.) and HOBT (1.1 eq.) were added to a solution of methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.07 M) in DMF. The reaction was stirred under N2 at RT overnight. The mixture was then partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with 1N HCl followed by brine, dried (Na2SO4), filtered and concentrated in vacuo. The product was used in the next step without further purification. (ES+) m/z 625 (M+H)+.
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