The synthesis of the thiophene analogue of dazoxiben - one of the most sele
ctive TXA(2)-synthase inhibitors - and its derivatization to a chlorinated,
more lipophilic product is described. The ethylenoxy moiety was introduced
via nucleophilic aromatic substitution of halogenated thiophene carboxylic
esters, the imidazol residue, by use of a t-butoxy group as a synthon afte
r ether cleavage and halogenation. Also, at this step chlorination of the t
hiophene moiety was carried out. After ester hydrolysis the target compound
s were obtained as hydrochlorides.