Optimized Synthesis of the O-Benzoylaminobenzoic Acid Derivative 2-Benzoylamino-N-[4-(4,6-Dimethylpyrimidin-2-Ylsulfamoyl)Phenyl]Benzamide Possessing Anxiolytic Activity

An optimized multi-step synthesis of a new highly effective and low-toxicity derivative of o -benzoylaminobenzoic acid amides possessing anxiolytic activity is presented. Anthranylamide and propionic anhydride instead of acetic anhydride were used as starting materials. The number of synthetic steps...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2021-12, Vol.55 (9), p.947-950
Main Authors: Kodonidi, I. P., Borovskii, B. V., Koval’, N. O., Kompantsev, V. A., Larskii, M. V., Chiryapkin, A. S.
Format: Article
Language:English
Subjects:
Acylation
Antianxiety agents
Comparative analysis
Hydrolysis
Medicine
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
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Summary:An optimized multi-step synthesis of a new highly effective and low-toxicity derivative of o -benzoylaminobenzoic acid amides possessing anxiolytic activity is presented. Anthranylamide and propionic anhydride instead of acetic anhydride were used as starting materials. The number of synthetic steps did not increase as compared to the known method because the hydrolysis of anthranylamide proceeded in an alkaline medium, in which the Schotten–Bauman acylation was carried out. The preparation of 2-benzoylamino- N -[4-(4,6-dimethylpyrimidin-2-ylsulfamoyl)phenyl]benzamide in the final step was modified by replacing the polar aprotic solvent DMF by the less toxic and more environmentally friendly DMSO. Use of more accessible and cost-effective starting materials in combination with Schotten–Bauman acylation, which eliminated environmentally hazardous benzene, was advisable for production of the active pharmaceutical ingredient. The developed laboratory procedure could be successfully used to obtain other biologically active compounds of o -benzoylaminobenzoic acid and their cyclic derivatives.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-021-02520-y