Synthesis of Some New Amides Derived from Indomethacin

ABSTRACT Indomethacin (1) was alb wed to react with thionyl chloride in dry benzene to yield [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl chloride (2) which was readily converted into a [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-(4-acetyl phenyl) acetamide (3) by its reaction with 4- amino acetophenone. Ethyl N-[{1-(4-chlorobenzoyl)-5-methoxy-2-methyl -1H- indol-3-yl} acetyl] glycinate (4) was synthesized by the reaction of acid chloride (2) with ethyl glycinate. The reaction of compound (3) with bromine in absolute ethanol afforded N-[4-(bromoacetyl) phenyl] - [1- (4-chlorobenzoyl) -5- methoxy -2- methyl -1H-indol-3-yl] acetamide(5). The compoundsN-[(4-(N-carboxymethyl) glycyl/ cystyl/ valinyl/ thereonyl/phenyl)1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl] acetamide (6-9) were synthesized by the reaction of compound (5) with amino acids. The structure of the synthesized compounds were confirmed by the available physical methods and some spectral data (I.R, U.V and 1H-NMR).