Reaction SMILES: [C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19].S(Cl)(Cl)(=O)=O.CCN(C(C)C)C(C)C>CC#N>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])(=[O:20])=[O:19]
Reactant: O=S(=O)(Cl)c1ccccn1
Reactant: CC(C)(C)OC(=O)NCCN
Solvent: CC#N
Solvent: CCN(C(C)C)C(C)C
Solvent: O=S(=O)(Cl)Cl
Product: CC(C)(C)OC(=O)NCCNS(=O)(=O)c1ccccn1
Temperature: 25 °C
Reaction time: 16 h
Yield: 80 %

Procedure:
Mono-N-Boc-ethylenediamine (860 mg, 5.37 mmol, 1 equiv) was reacted with pyridine-2-sulfonyl chloride. The appropriate sulfonyl chloride (1.2 equiv) was added to a solution of the amine (1 equiv) and DIPEA (2 equiv) in anhydrous CH3CN (0.1 M) at 0° C. The reaction was warmed to room temperature and stirred for 16 h, at which time the solvent was evaporated. The residue was re-dissolved in CH2Cl2, washed with 5% NaHCO3, water, brine, dried (Na2SO4), filtered and concentrated. After work-up, the crude material was dry-loaded onto silica gel, and purified by flash column chromatography (eluent CH2Cl2/MeOH/NH4OH, 92:7:1) to afford tert-butyl 2-(pyridine-2-sulfonamido)ethylcarbamate as a white powder (1.26 g, 80%): δH (400 MHz, DMSO-d6) 0.89 (s, 9H, C(CH3)3), 2.04 (m, 2H, SO2NHCH2CH2NHBoc), 2.86 (m, 2H, SO2NHCH2CH2NHBoc), 6.30 (br, 1H, NHSO2), 7.21 (m, 1H, CH (Py)), 7.414 (m, 1H, NHBoc), 7.47 (m, 1H, CH (Py)), 7.63, (m, 1H, CH (Py)), 8.27 (m, 1H, CH (Py)); δC (125 MHz, DMSO-d6) 28.0, 39.9, 42.5, 77.6, 121.4, 126.8, 138.5, 149.8, 155.3, 157.7; HRMS (ES+) calcd for [Cl2H19N3O4S+H] 302.1175. found 302.1174. The sulfonamide NH of tert-butyl 2-(pyridine-2-sulfonamido)ethylcarbamate (1.1 g, 3.65 mmol, 1 equi) was then chemoselectively alkylated with cyclohexylmethyl bromide (840 mg, 4.75 mmol, 1.3 equiv), but the reaction was stirred for 4 days at room temperature. To a solution of the sulfonamide (1 equiv) and Cs2CO3 (2 equiv) in DMF (0.1 M) at 0° C. was added the appropriate alkyl bromide or chloride (1.1 equiv). The resulting mixture was stirred at room temperature overnight. The reaction was diluted with water, then extracted into EtOAc (×3). The combined EtOAc extractions were washed with 5% NaHCO3 (×3), brine, dried (Na2SO4), filtered and concentrated. After work-up, the crude material was dry-loaded onto silica gel and purified by flash column chromatography (eluent CH2Cl2/MeOH/NH4OH, 92:7:1) to furnish tert-butyl 2-(N-(cyclohexylmethyl)pyridine-2-sulfonamido)ethylcarbamate in quantitative yield (1.53 g) as a white solid: δH (500 MHz, DMSO-d6) 0.77-0.83 (m, 2H, 2 CH (cyclohexylmethyl)), 1.09-1.19 (m, 3H, 3 CH (cyclohexylmethyl)), 1.36 (s, 9H, C(CH3)3), 1.54-1.65 (m, 6H, 6 CH (cyclohexylmethyl)), 3.03-3.07 (m, 4H, SO2NCH2CH2NHBoc, NCH2CH (cyclohexylmethyl)), 3.24 (t, J=7.0 Hz, 2H, SO2NCH2CH2NHBoc), 6.79 (br, 1H, NHBoc)), 7.67 (m, 1H, CH (Py)), 7.92 (m, 1H, CH (Py)), 8.09 (m, 1H, CH (Py)), 8.72 (m, 1H, CH (Py)); δC (125 MHz, DMSO-d6) 25.1, 25.8, 28.0, 29.9, 35.6, 39.9, 48.4, 55.4, 77.6, 122.1, 127.0, 138.6, 150.0, 155.3, 157.1; HRMS (ES+) calcd for [C19H31N3O4S+H] 398.2114. found 398.2113. tert-Butyl 2-(N-(cyclohexylmethyl)pyridine-2-sulfonamido)ethylcarbamate (1.28 g, 3.22 mmol, 1 equiv) was dissolved in propan-2-ol (15 mL). Upon complete dissolution of the solid, 4 M HCl (15 mL) was added, and the reaction was stirred for one hour. All solvents were then evaporated. The residue was re-dissolved in CH2Cl2 (250 mL) and carefully washed with saturated NaHCO3 (25 mL×3), dried (Na2SO4), filtered and concentrated to afford N-(2-aminoethyl)-N-(cyclohexylmethyl)pyridine-2-sulfonamide as a viscous oil (945 mg, 97%): δH (500 MHz, DMSO-d6) 0.78-0.84 (m, 2H, 2 CH (cyclohexylmethyl)), 1.09-1.17 (m, 3H, 3 CH (cyclohexylmethyl)), 1.57-1.68 (m, 6H, 6 CH (cyclohexylmethyl)), 2.75 (t, J=7.0 Hz, 2H, NCH2CH (cyclohexylmethyl)), 3.04 (t, J=7.4 Hz, 2H, SO2NCH2CH2NH2), 3.34 (t, J=7.4 Hz, 2H, SO2NCH2CH2NH2), 5.15 (br, 2H, NH2), 7.68 (m, 1H, CH (Py)), 7.93 (m, 1H, CH (Py)), 8.10 (m, 1H, CH (Py)), 8.73 (m, 1H, CH (Py)); δC (125 MHz, DMSO) 25.1, 25.8, 29.9, 35.7, 49.4, 55.5, 66.2, 122.2, 127.1, 138.7, 150.0, 157.1; HRMS (ES+) calcd for [Cl4H23N3O2S+H] 298.1589. found 298.1589.