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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

New Approaches to Endothelin Receptor Antagonist-Bosentan

Author(s): Pradeep Rebelli, Jayaprakash Rao Yerrabelly, Bharathi kumari Yalamanchili, Rajashekar Kommera, Venkat Reddy Ghojala and Kondal Reddy Bairy

Volume 10, Issue 5, 2013

Page: [364 - 368] Pages: 5

DOI: 10.2174/1570178611310050011

Price: $65

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.


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