Reaction SMILES: [CH2:1]([N:8]([CH2:29][CH:30]1[CH2:35][CH2:34][CH:33]([CH2:36][OH:37])[CH2:32][CH2:31]1)[S:9]([NH:12][C:13](=[O:28])[C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>ClCCl>[CH3:45][S:46]([O:37][CH2:36][CH:33]1[CH2:32][CH2:31][CH:30]([CH2:29][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[S:9]([NH:12][C:13](=[O:28])[C:14]2[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[C:16]([C:24]([F:25])([F:26])[F:27])[CH:15]=2)(=[O:11])=[O:10])[CH2:35][CH2:34]1)(=[O:48])=[O:47]
Reactant: O=C(NS(=O)(=O)N(Cc1ccccc1)CC1CCC(CO)CC1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
Reactant: CS(=O)(=O)Cl
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: CS(=O)(=O)OCC1CCC(CN(Cc2ccccc2)S(=O)(=O)NC(=O)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)CC1
Reaction time: 8 h
Yield: 91 %

Procedure:
Intermediate (4) (275 mg, 0.50 mmole, 1.0 eq) was dissolved in dichloromethane (2.5 mL), then treated with triethylamine (175 μL, 1.25 mmole, 2.5 eq) and methanesulfonyl chloride (43 μL, 0.55 mmole, 1.1 eq). The reaction was stirred overnight, then diluted with dichloromethane, washed with 5% aqueous citric acid followed by water, dried over sodium sulfate, filtered and evaporated to give the title compound in 91% yield. 1H NMR (500 MHz, DMSO-d6): δ 12.47 (s, 1H), 8.45 (s, 2H), 8.40 (s, 1H), 7.34 (d, 2H), 7.26 (t, 2H), 7.20 (m, 2H), 4.53 (s, 2H), 3.92 (d, 2H), 3.30 (water), 3.22 (d, 2H), 3.10 (s, 3H), 2.48 (DMSO), 1.63 (m, 4H), 1.53 (m, 1H), 1.37 (m, 1H), 0.77 (m, 4H). N-{[4-(azidomethyl)cyclohexyl]methyl}-N-benzyl-N′-[3,5-bis(trifluoromethyl)benzoyl]sulfamide (21): Mesylate (20) (283 mg, 0.45 mmole, 1.0 eq) was dissolved in N,N-dimethylformamide (3 mL) and sodium azide (292 mg, 4.5 mmole, 10.0 eq) was added. CAUTION: SODIUM AZIDE IS EXPLOSIVE. The reaction was heated to 90° C. overnight. The reaction mixture was then diluted with ethyl acetate and washed twice with water and 3× with brine. The organic was dried over sodium sulfate, filtered and evaporated to give the title compound in nearly quantitative yield. 1H NMR (500 MHz, DMSO-d6): δ 12.47 (s, 1H), 8.45 (s, 2H), 8.17 (s, 1H), 7.36 (d, 2H), 7.25 (t, 2H), 7.18 (m, 2H), 4.39 (s, 2H), 3.30 (water), 3.08(d, 2H), 2.96 (d, 2H), 2.48 (DMSO), 1.60 (m, 4H), 1.22 (m, 2H), 0.65 (m, 4H). N-{[4-(aminomethyl)cyclohexyl]methyl}-N-benzyl-N′-[3,5-bis(trifluoromethyl)benzoyl]sulfamide (22): Azide (21) (254 mg, 0.44 mmole, 1.0 eq) was dissolved in methanol (2.2 mL), then the vessel was evacuated and charged with nitrogen. 10% Palladium on carbon (93 mg, 88 μmole, 0.2 eq) was added to the reaction, then the vessel was evacuated and charged with hydrogen gas. Reaction was deemed complete at 4.5 hours. Catalyst was filtered off over a pad of celite and the filtrate was evaporated. The crude product was reconstituted in 1,4-dioxane, then 4N hydrogen chloride in dioxane (180 μL, 720 μmole, 1.6 eq) was added and the solution diluted with ether until the amine hydrochloride salt precipitated out. This was filtered, then the filtrate was evaporated and taken up in 1 ml dioxane. It was diluted again with ether, and a second crop of the amine hydrochloride was obtained. 1H NMR (500 MHz, DMSO-d6): δ 12.49 (s, 1H), 8.46 (s, 2H), 8.40 (s, 1H), 7.89 (s, 3H), 7.35 (d, 2H), 7.26 (t, 2H), 7.19 (m, 2H), 4.52 (s, 2H), 3.30 (water), 3.23 (d, 2H), 2.53 (t, 2H), 2.48 (DMSO), 1.65 (m, 4H), 1.38 (m, 2H), 0.71 (m, 4H).