Reaction SMILES: [CH2:1]([N:8]1[CH2:14][CH:13]([NH:15][S:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([Cl:29])[CH:25]=3)[CH:20]=2)(=[O:18])=[O:17])[C:12](=[O:30])[N:11]([C:31]2[CH:36]=[CH:35][C:34](Br)=[CH:33][CH:32]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)C=C(S(Cl)(=O)=O)C=[CH:42]2.[N:53]1[CH:58]=CC=C[CH:54]=1>ClCCl>[CH2:1]([N:8]1[CH2:14][CH:13]([NH:15][S:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([Cl:29])[CH:25]=3)[CH:20]=2)(=[O:18])=[O:17])[C:12](=[O:30])[N:11]([C:31]2[CH:36]=[CH:35][C:34]([C:46]3[CH:47]=[CH:48][CH:39]=[CH:40][C:41]=3[CH2:42][N:53]([CH3:58])[CH3:54])=[CH:33][CH:32]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: O=S(=O)(Cl)c1ccc2cc(Cl)ccc2c1
Reactant: O=C1C(NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)CN(Cc2ccccc2)CCN1c1ccc(Br)cc1
Reactant: c1ccncc1
Solvent: ClCCl
Product: CN(C)Cc1ccccc1-c1ccc(N2CCN(Cc3ccccc3)CC(NS(=O)(=O)c3ccc4cc(Cl)ccc4c3)C2=O)cc1
Reaction time: 5 h

Procedure:
Part A. 1-Benzyl-4-(4-bromo-phenyl)-[1,4]diazepan-5-one: Commercially available 1-benzyl-(1,4)-diazepan-5-one (14.7 mmol), p-bromoiodobenzene (1 eq), 4,5-bis(diphenyl-phosphino)-9,9-dimethylxanthene (0.15 eq), cesium carbonate (1.5 eq), and palladium acetate (0.1 eq) were placed in a round bottom flask and it was evacuated and flushed 3× with nitrogen. To this mixture was then added 200 mL of dioxane and the resulting solution was again evacuated and flushed 3× times with nitrogen gas. The mixture was allowed to stir at 75° C. overnight during which time the mixture turned from brown to bright yellow suspension. The mixture was cooled and diluted with dichloromethane and then was filtered through a pad of celite. The filtrate was removed under reduced pressure and the residue was purified by flash column chromatography eluting with 50% EtOAc/Hex to give compound 1 as an off-white solid (63%). Mass spectrum, ESI (M+H) 359.3, 361.3. Part B. 6-Azido-1-benzyl-4-(4-bromo-phenyl)-[1,4]diazepan-5-one: To a solution of diisopropylamine (1.3 eq) in 1 mL THF at −78° C. was added 2.5 n-BuLi (1.3 eq) dropwise. After stirring at −78° C. for 15 min, a solution of the compound of Ex. 77, Part A (0.56 mmol) in 1 mL of THF was added dropwise. After another 15 min, a solution of trisyl azide (1.3 eq) in 1 mL THF was added and stirring was continued for another 5 min before acetic acid (1.3 eq) was added. The reaction was allowed to warm to room temperature overnight. The mixture was diluted with saturated ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried (MgSO4), filtered and concentrated under vacuo to give a yellow residue which was purified by flash column chromatography eluting with 30% EtOAc:Hex to give the azide product as an oil (63%). Mass spectrum, ESI (M+H) 400.3, 402.3. Part C. 6-Amino-1-benzyl-4-(4-bromo-phenyl)-[1,4]diazepan-5-one: A solution of the compound of Ex. 77, Part B (0.19 mmol) in 2 mL methanol was added slowly to a stirred suspension of SnCl2 (2 eq) in 1 mL of methanol at 0° C. The mixture was allowed to warm to room temperature after the addition was over and stirring was continued overnight. Methanol was then removed under reduced pressure and the residue was diluted with cold water and made alkaline with 1N NaOH solution. Dichloromethane was added and the biphasic solution was filtered through a sintered glass funnel. The layers were then separated and the aqueous layer was saturated with brine and re-extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated to give the amine as an oil (86%). Mass spectrum, ESI (M+H) 374.3, 376.3. Part D. 6-Chloro-naphthalene-2-sulfonic acid [1-benzyl-4-(4-bromo-phenyl)-5-oxo-[1,4]diazepan-6-yl]-amide: To a solution of the compound of Ex. 77, Part C (0.16 mmol) in 2 mL dichloromethane was added 6-chloronapthalene-2-sulfonyl chloride (1.3 eq) then pyridine (3 eq) at room temperature. After stirring for an additional 5 hours, the excess reagent and solvent were evaporated off and then the residue was purified by flash column chromatography eluting with 0-2% MeOH/CHCl3 to give the sulfonamide product as a clear film (75%). Mass spectrum, ESI (M+H) 598.3, 600.3. Part E. 6-Chloro-naphthalene-2-sulfonic acid {1-benzyl-5-oxo-4-[2′-(2-oxo-ethyl)-biphenyl-4-yl]-[1,4]diazepa n-6-yl}-amide: The compound of Ex. 77, Part D (0.12 mmol), 2-formylbenzeneboronic acid (1.5 eq), potassium carbonate (4 eq), and tetrakis(triphenylphosphine)palladium(0) (10 mol %) were placed in a round bottom flask and evacuated and flushed twice with N2. To this mixture was added 2:1 toluene/ethanol (9 mL) and the resulting mixture was evacuated and flushed again with N2 (2×). The mixture was allowed to heated to reflux for two hours. The solution was then cooled to room temperature, diluted with water and extracted two times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a brown residue which was purified by flash column chromatography eluting with 30% EtOAc:Hex to give the product as a clear film (73%). Mass spectrum, ESI (M+H) 624.4, 626.4. Part F. 6-Chloro-naphthalene-2-sulfonic acid [1-benzyl-4-(2′-dimethylaminomethyl-biphenyl-4-yl)-5-oxo-[1,4]d iazepan-6-yl]-amide: To a solution of the compound of Ex. 77, Part E (0.09 mmol) and dimethylamine hydrochloride (3 eq) in 3 mL of dichloroethane was added diisoproylethylamine (3 eq). After stirring at room temperature for 15 min, sodium triacetoxyborohydride (3 eq) was added to the mixture. After stirring at room temperature overnight, the mixture was diluted with water and extracted two times with chloroform. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the crude product as a yellow film which was purified by column chromatography eluting with 5% MeOH:CHCl3 to give the target as a foam (73%). 1H NMR (CDCl3, 300 MHz) δ 8.44 (s, 1H), 7.92 (m, 2H), 7.85 (s, 2H), 7.55 (m, 2H), 7.30 (m, 8H), 7.17 (d, JL=7.5 Hz, 1H), 6.96 (d, J=8.4 Hz, 2H), 6.37 (br d, J=5.1 Hz, 1H), 4.36 (br s, 1H), 3.87 (m, 1H), 3.67 (dd, J=36.1, 13.4 Hz, 2H), 3.60 (br m, 1H), 3.30 (s, 2H), 3.50 (br m, 1H), 2.90 (m, 1H), 2.52 (m, 2H), 2.14 (s, 6H); mass spectrum, ESI (M+H) 653.5, 655.5.