(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide → (RS)-N-{4-Carbamimidoyl-2-[(2-diethylamino-ethylcarbamoyl)-methoxy]-benzyl}-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide hydrochloride

Participants

Reaction Steps

In analogy to example 16.4, (RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide (example 126.1) was alkylated with 3-(chloromethyl)-1,2,4-oxadiazole/cesium carbonate in DMF to give a mixture of N-[4-cyano-2-([1,2,4]oxadiazol-3-ylmethoxy)-benzyl]-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide and N-(4-cyano-2-cyanomethoxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide. These compounds were converted according to general procedure D to give (RS)-N-{4-Carbamimidoyl-2-[(2-diethylamino-ethylcarbamoyl)-methoxy]-benzyl}-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide hydrochloride.

Provenance & Evidence