Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

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Synthesis and characterization of process related impurities of an antituberculosis drug-Prothionamide

Author(s): Kalyana Chakravarthi Eadaraa,b, Srinivasa Rao V. N. Divvelaa, Sachin B. Sawanta, Shailesh W. Gohada, Shailendra Kumar Sinhaa, Pratap Reddy Padia and Rajendra Agarwala

The synthesis of 7 contaminants of prothionamide 4a formed during the preparation of prothionamide bulk drug, is described. The products are 2,6–dipropylpyridine-4-carbothioamide 4b, 3-propylpyridine-4-carbothioamide 4c, 2- ethylpyridine-4-carbothioamide 4d, 2-propylisonicotinamide 6, pyridine-4-carbothioamide 4e, 2- propylisonicotinicacid 5, prothionamide sulfoxide 7. Unknown Compounds of 4c and 5-7 were isolated and characterized for the first time. The side products formed during the synthesis of prothionamide intermediate 2- propyl-4-cyanopyridine 3a were also synthesized and characterized as 2,6-dipropyl-4-cyanopyridine 3b, 3-propyl-4- cyanopyridine 3c, 2-ethyl-4-cyanopyridine 3d. The structures of all these compounds were established on the basis of spectral data (IR, 1H-NMR and MS).


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