Reaction SMILES: C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[CH:20]1([C:26]2[C:27]3[CH:28]=[CH:29][C:30]([C:57](O)=[O:58])=[CH:31][C:32]=3[N:33]3[CH2:39][C:38]([C:40]([N:42]4[CH:47]5[CH2:48][CH2:49][CH:43]4[CH2:44][N:45]([CH3:50])[CH2:46]5)=[O:41])=[CH:37][C:36]4[CH:51]=[C:52]([O:55][CH3:56])[CH:53]=[CH:54][C:35]=4[C:34]=23)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[CH:60]1([CH2:63][C:64]2([S:67]([NH2:70])(=[O:69])=[O:68])[CH2:66][CH2:65]2)[CH2:62][CH2:61]1.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[CH:20]1([C:26]2[C:27]3[CH:28]=[CH:29][C:30]([C:57]([NH:70][S:67]([C:64]4([CH2:63][CH:60]5[CH2:61][CH2:62]5)[CH2:65][CH2:66]4)(=[O:68])=[O:69])=[O:58])=[CH:31][C:32]=3[N:33]3[CH2:39][C:38]([C:40]([N:42]4[CH:43]5[CH2:49][CH2:48][CH:47]4[CH2:46][N:45]([CH3:50])[CH2:44]5)=[O:41])=[CH:37][C:36]4[CH:51]=[C:52]([O:55][CH3:56])[CH:53]=[CH:54][C:35]=4[C:34]=23)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1
Reactant: NS(=O)(=O)C1(CC2CC2)CC1
Reactant: COc1ccc2c(c1)C=C(C(=O)N1C3CCC1CN(C)C3)Cn1c-2c(C2CCCCC2)c2ccc(C(=O)O)cc21
Agent: O=C(n1ccnc1)n1ccnc1
Solvent: C1CCOC1
Solvent: CCOC(C)=O
Solvent: C1CCC2=NCCCN2CC1
Product: COc1ccc2c(c1)C=C(C(=O)N1C3CCC1CN(C)C3)Cn1c-2c(C2CCCCC2)c2ccc(C(=O)NS(=O)(=O)C3(CC4CC4)CC3)cc21
Temperature: 60 °C
Reaction time: 0.08 h
Yield: 35.4 %

Procedure:
CDI (27 mg, 0.17 mmol) was added to a stirring solution of 13-cyclohexyl-3-methoxy-6-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid trifluoroacetate (70 mg, 0.130 mmol)) in THF (0.5 mL) and the reaction mixture was heated at 60° C. for 1.5 h. The reaction was cooled to rt and then 1-(cyclopropylmethyl)cyclopropane-1-sulfonamide (29.6 mg, 0.169 mmol) was added. The reaction was stirred 5 min. and then DBU (0.029 mL, 0.195 mmol) was added. The reaction was stirred at rt for 1 h, more DBU (0.029 mL, 0.195 mmol) was added and stirred at rt ON (˜75% conversion by LCMS). The reaction was diluted with EtOAc (˜2 mL) and washed with 1M aq. HCl (2×2 mL). The organic layer was concentrated under a steam of nitrogen, dissolved into MeOH (˜3 mL) and purified by preparative HPLC (Column: Xterra Prep MS C18 5 u 30×100 mm, Eluent A: 5% acetonitrile/water with 10 mM ammonium acetate, Eluent B: 95% acetonitrile/water with 10 mM ammonium acetate, Flow Rate: 42 mL/min, linear gradient from 15% Eluent B to 100% Eluent B over 20 min) to yield 13-cyclohexyl-N-((1-(cyclopropylmethyl)cyclopropyl)sulfonyl)-3-methoxy-6-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-7H-indolo[2,1-a][2]benzazepine-10-carboxamide (32 mg, 0.046 mmol, 35% yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 0.02-0.09 (m, 2H), 0.38-0.47 (m, 2H), 0.61-0.74 (m, 1H), 1.14-2.95 (m, 31H), 3.89 (s, 3H), 4.20-4.42 (m, 1H), 5.11-5.32 (m, 1H), 6.82 (s, 1H), 6.86-6.90 (m, 2H), 7.05 (dd, J=8.8, 2.6 Hz, 1H), 7.49 (d, J=8.8 Hz, 1H), 7.49-7.54 (m, 1H), 7.86 (d, J=8.4 Hz, 1H), 8.10 (br s, 1H). LC-MS retention time: 3.46 min; m/z 697 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10 u C18 3.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.