5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-3-methylpyrazine-2-carboxylic acid, methyl ester → 2,3-Dichloro-N-[5-(hydroxymethyl)-3-methoxy-6-methyl-2-pyrazinyl)benzenesulphonamide

Participants

Reaction Steps

To a stirred solution of 5-(2,3-dichlorobenzenesulphonylamino)-6-methoxy-3-methylpyrazine-2-carboxylic aicd, methyl ester (Example 119) (0.19 g) in tetrahydrofuran (10 mL) under an atmosphere of nitrogen was added a solution of lithium triethylborohydride (1.7 mL of a 1M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for 1 h, before quenching with aqueous ammonium chloride and extraction into dichloromethane. The organic phase was dried (MgSO4), filtered and evaporated to give the crude product as a colourless oil. Chromatography on silica gel eluting with dichloromethane/ethyl acetate/acetic acid (150:50: 1) gave the title compound as a white solid (0.38 g).

Provenance & Evidence