Synthesis of Some New Amides Derived from Indomethacin

Al-Naimi, Kawther; Alwahb, Haitham A.; Younis, Hyffaa

doi:10.33899/edusj.2013.163060

	Synthesis of Some New Amides Derived from Indomethacin
Journal of Education and Science
Article 11, Volume 26, Issue 5, 2013, Pages 105-112 PDF (441.65 K)
Document Type: Research Paper
DOI: 10.33899/edusj.2013.163060
Authors
Kawther Al-Naimi^* ¹; Haitham A. Alwahb²; Hyffaa younis^* ²
¹Department of Chemistry, College of Science, University of Mosul
²Department of Chemistry, College of science, University of Mosul
Abstract
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).
Keywords
Indomethacin; indomethacin amide and amino acids

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