Pyridine → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(2-tert-butylsulfamoyl-ethyl)-2-cyclohex-1-enyl-phenyl]-amide

Participants

Reaction Steps

To a suspension of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 11, step (d), 228 mg, 0.746 mmol) and pyridine (66 μL, 0.81 mmol) in DCM (5 mL), SOCl2 (60 μL, 0.81 mmol) was added at 0° C. The resulting mixture was stirred at RT for 1 h and transferred to a mixture of 2-(4-amino-3-cyclohex-1-enyl-phenyl)-ethanesulfonic acid tert-butylamide (as prepared in the previous step, 228 mg, 0.670 mg) and pyridine (66 μL, 0.81 mmol) in DCM (5 mL) at 0° C. The resulting mixture was stirred at RT over night. Water (20 mL) was then added and organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (20-50% EtOAc/hexane) to obtain the title compound (271 mg, 68%). Mass spectrum (ESI, m/z): Calcd. for C29H43N5O4SSi, 586.2 (M+H), found 586.0.

Provenance & Evidence