Abstract
An improved and efficient synthetic process developed for an endothelin receptor antagonist, bosentan monohydrate by condensing a key intermediate 4-tert-butyl-N-(6-hydroxy-5-(2-methoxyphenoxy)-2,2’-bipyrimidine-4- yl)benezenesulfonamide 5 with commercially cheaper chloro acetonitrile and α-halo esters. This synthetic approach efficiently provides highly pure bosentan without formation of the major impurity 2 (dimer) and less than 0.15% of Nalkylated impurity 3 and pyrimidinone impurity 5 in the final product. In the present process upon purification of bosentan monohydrate gave overall yield of 62-65%.
Keywords: Pyrimidinone, chloro acetonitrile, α-halo esters, bosentan monohydrate.
Letters in Organic Chemistry
Title:New Approaches to Endothelin Receptor Antagonist-Bosentan
Volume: 10 Issue: 5
Author(s): Pradeep Rebelli, Jayaprakash Rao Yerrabelly, Bharathi kumari Yalamanchili, Rajashekar Kommera, Venkat Reddy Ghojala and Kondal Reddy Bairy
Affiliation:
Keywords: Pyrimidinone, chloro acetonitrile, α-halo esters, bosentan monohydrate.
Abstract: An improved and efficient synthetic process developed for an endothelin receptor antagonist, bosentan monohydrate by condensing a key intermediate 4-tert-butyl-N-(6-hydroxy-5-(2-methoxyphenoxy)-2,2’-bipyrimidine-4- yl)benezenesulfonamide 5 with commercially cheaper chloro acetonitrile and α-halo esters. This synthetic approach efficiently provides highly pure bosentan without formation of the major impurity 2 (dimer) and less than 0.15% of Nalkylated impurity 3 and pyrimidinone impurity 5 in the final product. In the present process upon purification of bosentan monohydrate gave overall yield of 62-65%.
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Cite this article as:
Rebelli Pradeep, Yerrabelly Jayaprakash Rao, Yalamanchili Bharathi kumari, Kommera Rajashekar, Ghojala Venkat Reddy and Bairy Kondal Reddy, New Approaches to Endothelin Receptor Antagonist-Bosentan, Letters in Organic Chemistry 2013; 10 (5) . https://dx.doi.org/10.2174/1570178611310050011
DOI https://dx.doi.org/10.2174/1570178611310050011 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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