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Synlett 2014; 25(2): 265-269
DOI: 10.1055/s-0033-1340281
letter
© Georg Thieme Verlag Stuttgart · New York

An Alternate Synthesis of Bosentan Monohydrate, an Endothelin Receptor Antagonist[1]

Rebelli Pradeep
a   Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad 500004, India   Email: yjpr_19@yahoo.com
b   Department of Chemistry, Jawaharlal Nehru Technological University College of Engineering, Hyderabad 500085, India
c   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Andhra Pradesh 502307, India
,
Yerrabelly Jayaprakash Rao*
a   Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad 500004, India   Email: yjpr_19@yahoo.com
,
Yalamanchili Kumari Bharathi
b   Department of Chemistry, Jawaharlal Nehru Technological University College of Engineering, Hyderabad 500085, India
,
Porala Subbanarsimulu
c   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Andhra Pradesh 502307, India
,
Ghojala Venkat Reddy
c   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Andhra Pradesh 502307, India
,
Bairy Kondal Reddy
c   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Andhra Pradesh 502307, India
› Author Affiliations
Further Information

Publication History

Received: 16 August 2013

Accepted after revision: 14 October 2013

Publication Date:
02 December 2013 (online)

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Abstract

An alternate synthesis of an endothelin receptor antagonist bosentan monohydrate is reported. This new synthetic route involves the coupling of p-tert-butyl-N-[6-chloro-5-(2-methoxy-phenoxy)(2,2′-bipyrimidin)-4-yl]benzene sulfonamide with commercially available raw material (2,2-dimethyl-1,3-dioxolan-4-yl)methanol as the key step. Attractive features of this approach are its versatileness, commercial availability of raw materials, usage of eco-friendly reagents, and it efficiently provides the desired bosentan monohydrate free from reported impurities such as dimer, N-alkylated, and pyrimidinone impurities.

Key words

alternate synthesis - bosentan monohydrate - eco-friendly reagents - dimer impurity - N-alkylated - pyrimidinone

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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