O[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9]CN=C=NCCCN(C)C.[C:20]([CH2:23][N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]([NH:34][C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42](Cl)=[CH:41][CH:40]=3)=[O:36])[C:25]1=[O:47])([OH:22])=[O:21]>C(Cl)Cl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:22][C:20](=[O:21])[CH2:23][N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH:26]([NH:34][C:35]([C:37]2[NH:38][C:39]3[C:44]([CH:45]=2)=[CH:43][C:42]([CH3:9])=[CH:41][CH:40]=3)=[O:36])[C:25]1=[O:47]N-Hydroxysuccinimide (496 mg, 4.31 mmol) and EDCI (1.04 g, 5.38 mmol) were added to a suspension of N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloroindole-2-carboxamide (Example 2, 1.71 g, 4.31 mmol)) in DCM (50 mL) and stirred for 18 hours. The suspension was evaporated and the residue partitioned between EtOAc:THF (4:1)(200 mL) and H2O. The organic was dried (Na2SO4), filtered and evaporated. The solid was triturated with refluxing Et2O (25 mL), filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford the title compound (2.08 g, 98%) as a pale brown powder.
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