Patent ID: 7009057

Claim:
A method for obtaining the antidiabetic of formula I comprising condensing a compound of formula III where Z is a leaving group with a compound of formula II where R 1 is a protecting group to form an ether of formula IV: removing protecting group R 1 from formula IV to form an aniline of formula V: converting the aniline of formula V to a diazonium salt, reacting the diazonium salt with an olefin of formula VI where R 2 is an electron withdrawing group to form an alkyl halide of formula VII: reacting the alkyl halide of formula VII with thiourea to form an imine of formula VIII: and, hydrolyzing the imine of formula VIII to give the antidiabetic of formula I; wherein the leaving group Z is a radical of the formula wherein A, which may be substituted or unsubstituted, is an aryl or an alkyl group; wherein M is hydrogen or an alkali metal; wherein the protecting group R 1 is selected from the group consisting of an acyl group derived from lower aliphatic acids (C 1 –C 4 ), an acyl group derived from lower aromatic acids, n-alkyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, 9-fluorenylmethyloxycarbonyl, alloxycarbonyl, 2-cyanoethoxycarbonyl, dimethylaminomethylenyl, and hexa-2,4-dien-2,5-diyl; wherein m is 0 or 1; wherein when m=1, R=Br; wherein the electron withdrawing group R 2 is selected from the group consisting of a cyano group, a carboxylic acid, an ester, and the salt of a carboxylic acid; and wherein X is a halogen atom.