Dimethylsulphamoyl chloride → HCID 11154007, compound

Participants

Reaction Steps

DMAP (80.1 mg, 0.65 mmol) was added to a solution of 1-(cyclohexylmethyl)-2-(1,1-dimethylpropyl)-1H-benzimidazol-5-amine (69.5 mg, 0.18 mmol) (for preparation, see the following steps B, C, D, E and F) in acetonitrile (10 mL) at 0° C., followed by addition of dimethylsulfamoyl chloride (22 uL, 28.7 mg, 0.20 mmol). The resulting mixture was heated at reflux for 20 h and then quenched with MeOH (2 mL). After evaporation of the solvent, the residue was dissolved in EtOAc (100 mL) and washed with NaCl aqueous solution (10 mL) and dried over Na2SO4. After filtration and evaporation, the residue was purified by MPLC (hexanes/EtOAc 1:1 as eluent on silica gel) to give the title compound as a white solid (56.2 mg, 76%), which was converted to a white solid as a TFA salt. 1H NMR (400 MHz, CD3OD): δ 0.84 (t, J=7.52 Hz, 3H), 1.24 (m, 5H), 1.64 (m, 2H), 1.66 (s, 6 μl), 1.71 (m, 1H), 1.78 (m, 2H), 2.01 (q, J=7.55 Hz, 2H), 2.11 (m, 1H), 2.82 (s, 6H), 4.44 (d, J=7.81 Hz, 2H), 7.37 (dd, J=8.98, 2.15 Hz, 1H), 7.69 (d, J=2.15 Hz, 1H), 7.84 (d, J=8.98 Hz, 1H); MS (ESI) (M+H)+: 407.3; Anal. Calcd for C21H34N4O2S+1.0 TFA+0.2 H2O: C, 52.70; H, 6.81; N, 10.69. Found: C, 52.70; H, 6.66; N, 10.45.

Provenance & Evidence