Reaction SMILES: [O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[N:22][C:23]5[C:28]([N:29]=4)=[CH:27][C:26]([C:30](O)=[O:31])=[CH:25][CH:24]=5)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:5]2[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=2[NH:3]1.C1C=CC2N(O)N=NC=2C=1.N=C=N.[CH2:56]([N:58]([CH2:62][CH3:63])[CH2:59][CH2:60][NH2:61])[CH3:57].CN1[C:69](=[O:70])CCC1>CN1C(=O)CCC1.C(Cl)Cl.CCN(C(C)C)C(C)C.C(Cl)Cl>[CH2:56]([N:58]([CH2:62][CH3:63])[CH2:59][CH2:60][NH:61][C:30]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]3[CH2:9][CH2:8][CH:7]([N:6]4[C:5]5[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=5[NH:3][C:2]4=[O:1])[CH2:12][CH2:11]3)=[CH:15][CH:16]=1)=[N:29]2)=[O:31])[CH3:57].[CH2:56]([N:58]([CH2:62][CH3:63])[CH2:59][CH2:60][NH:61][C:69]([C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[N:29]=[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:10]3[CH2:9][CH2:8][CH:7]([N:6]4[C:5]5[CH:39]=[CH:40][CH:41]=[CH:42][C:4]=5[NH:3][C:2]4=[O:1])[CH2:12][CH2:11]3)=[CH:15][CH:16]=1)[C:21]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[N:22]2)=[O:70])[CH3:57]
Reactant: CN1CCCC1=O
Reactant: O=C(O)c1ccc2nc(-c3ccccc3)c(-c3ccc(CN4CCC(n5c(=O)[nH]c6ccccc65)CC4)cc3)nc2c1
Reactant: CCN(CC)CCN
Agent: N=C=N
Agent: On1nnc2ccccc21
Solvent: ClCCl
Solvent: CCN(C(C)C)C(C)C
Product: CCN(CC)CCNC(=O)c1ccc2nc(-c3ccc(CN4CCC(n5c(=O)[nH]c6ccccc65)CC4)cc3)c(-c3ccccc3)nc2c1
Product: CCN(CC)CCNC(=O)c1ccc2nc(-c3ccccc3)c(-c3ccc(CN4CCC(n5c(=O)[nH]c6ccccc65)CC4)cc3)nc2c1

Procedure:
The mixture of 3-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylquinoxaline-6-carboxylic acid (7-1) and 2-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-phenylquinoxaline-6-carboxylic acid (7-1), 222 mg (0.4 mmol) was dissolved in NMP/DCM/DIEA (10 mL, 9/1). To this solution was added HOBt (152 mg, 1.0 mmol), PS-carbodiimide (1.1 g, 1.3 mmol), and DCM (5 mL). The resultant mixture was shaken 0.5 h. After this time, N,N-diethylethane-1,2-diamine (232 mg, 2.0 mmol) was added to the NMP solution and the reaction was shaken over weekend. After this time, LCMS indicated that the coupling reaction was complete. The resin was filtered and washed with MeOH (3×15 mL). The combined solution was dried to give a brown residue. This residue was then purified on an Agilent 1100 series Mass Guided HPLC purification system to afford the two pure regioisomers N-[2-(diethylamino)ethyl]-3-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylquinoxaline-6-carboxamide (7-2) (50.7 mg) and N-[2-(diethylamino)ethyl]-2-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-phenylquinoxaline-6-carboxamide (7-3) (119 mg). Analytical data for N-[2-(diethylamino)ethyl]-3-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-2-phenylquinoxaline-6-carboxamide (7-2): Analytical LCMS: single peak (214 nm) at 2.084 min (CH3CN/H2O/1% TFA, 4 min gradient). 1H NMR (500 MHz, DMSO-d6): δ 10.96 (s, 1H), 10.10 (s, 1H), 9.50 (s, 1H), 9.20 (t, J=5.9 Hz, 1H), 8.69 (s, 1H), 8.26–8.34 (m, 2H), 7.49–7.66 (m, 6H), 7.35–7.47 (m, 3H), 7.26–7.32 (m, 1H), 6.97–7.04 (m, 3H), 4.48–4.58 (m, 1H), 4.40 (s, 2H), 3.72 (q, J=6.1 Hz, 2H), 3.50 (d, J=11.7 Hz, 2H), 3.34(q, J=5.4 Hz, 2H), 3.20–3.30 (m, 6H), 2.67 (q, J=14.5 Hz, 2H), 1.96 (d, J=13.0 Hz, 2H), 1.25 (t, J=7.5 Hz, 6H). HRMS, calc'd for C40H44N7O2 (M+H), 654.3551; found 654.3573.