3-Bromopentane → (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(1-ethyl-propoxy)-2,6-difluoro-phenyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution under Ar of (RS)-N-(4-cyano-benzyl)-2-(2,6-difluoro-3-hydroxy-phenyl)-2-ethoxy-acetamide (200 mg) in DMF (10 ml) was added CSCO3 (226 mg) and 3-bromopentane (105 mg). The solution was stirred over night at 80° C. The solvent was evaporated and the residue was taken up in H2O (50 ml). The product was extracted with AcOEt (2×100 ml). The organic layers were washed with H2O (2×50 ml) and dried (NaaSO4) and the solvent was evaporated. CC (AcOEt/Hept 2:3 to AcOEt) afforded 190 mg (79%) of (RS)-N-(4-cyano-benzyl)-2-ethoxy-2-[3-(1-ethyl-propoxy)-2,6-difluoro-phenyl]-acetamide. This material was converted to (RS)-N-(4-carbamimidoyl-benzyl)-2-ethoxy-2-[3-(1-ethyl-propoxy)-2,6-difluoro-phenyl]-acetamide acetate by the sequence of procedures G and H. Off-white solid. MS 434.4 ([M+H]+).

Provenance & Evidence