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CC BY-NC-ND 4.0 · SynOpen 2020; 04(03): 62-65
DOI: 10.1055/s-0040-1707267
paper

Expedient Approach to the Synthesis of Betrixaban

Chada Raji Reddy  ∗
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Sudam N. Sinare
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
› Author AffiliationsC.R.R. is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi for financial support as part of mission mode project (INPROTICS; HCP 011).
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Abstract

A new scalable route to synthesize the factor Xa (FXa) inhibitor betrixaban is disclosed. The product is obtained in a seven-step reaction sequence (in five stages using two one-pot reactions) starting from easily accessible 4-(N,N-dimethylcarbamimidoyl)benzoate. Effective isolation of intermediates, use of cost-effective amide formation and 2-methyltetrahydrofuran as an effective reaction solvent as well as for extraction in three of the stages, are key features. The strategy provides the desired product in 38% overall yield with high purity (>98%).

Key words

betrixaban - factor Xa (FXa) inhibitor - anticoagulant - one-pot reaction - amidation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707267.
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Publication History

Received: 29 July 2020

Accepted after revision: 17 August 2020

Article published online:
04 September 2020

© 2020. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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