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. 2016 Mar 11;59(7):3183–3203. doi: 10.1021/acs.jmedchem.5b01963

Scheme 3. Synthesis of Sulfonamide, Acylsulfonamide, Sulfonylurea, and Acylurea Derivatives.

Scheme 3

Reagents and Reaction Conditions: (a) MsCl, NEt3, CH2Cl2, 4 °C, 24 h, (88%); (b) methanesulfonamide, EDCI·HCl, DMAP, CH2Cl2, 45 °C, 8 h, then r.t., 48 h, (70%); (c) (i) 4 M HCl in dioxane, r.t., 5 min; (ii) CDI, DMF, CH3CN, r.t., 2 h; (iii) NaH, methanesulfonamide, DMF, r.t., 16 h, (11%); (d) (i) TBTU, DIEA, CH2Cl2, r.t., 25 min; (ii) N,N-dimethylsulfamide, r.t., 14 h, (81%); (e) Ac2O, CH2Cl2, 50°C, 24 h, then r.t., 48 h, (75%).