Small change for big improvement in the preparation of the key intermediate N1, N3-disubstituted 1,3,5-triazone of ensitrelvir

Wei Hu; Yuanchang Liu; Xiang Zhang; Panpan Zheng; Feifei Yang; Guangyang Guo; Xin Xie; Jiuzhong Huang; Weiming Chen

doi:10.1039/D2RA07844A

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Small change for big improvement in the preparation of the key intermediate N¹, N³-disubstituted 1,3,5-triazone of ensitrelvir†

Wei Hu,‡^a Yuanchang Liu,‡^a Xiang Zhang,^a Panpan Zheng,

^a Feifei Yang,^a Guangyang Guo,^a Xin Xie,^ab Jiuzhong Huang

*^ab and Weiming Chen

*^ab

Author affiliations

* Corresponding authors

^a School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou 341000, P. R. China
E-mail: wader_chen@163.com

^b Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, Gannan Medical University, Ganzhou 341000, P. R. China

Abstract

In this study, the key intermediate N¹, N³-disubstituted 1,3,5-triazone of ensitrelvir fumaric acid, approved in Japan for the treatment of SARS-CoV-2 infection under the emergency regulatory approval system, was produced from S-ethylisothiourea hydrobromide and aminomethyl triazole with CDI by four-step telescoped strategy including CDI-activated, condensation, CDI-cyclization, and N¹-alkylation. The strategy with simple conditions and operations had a total yield of 53% on a gram scale. The strategy for synthesizing the key N¹, N³-disubstituted 1,3,5-triazone intermediate of ensitrelvir might provide a new avenue for further research and development of ensitrelvir analogs.

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Article information

DOI: https://doi.org/10.1039/D2RA07844A
Article type: Paper
Submitted: 08 Dec 2022
Accepted: 14 Jan 2023
First published: 25 Jan 2023
This article is Open Access

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RSC Adv., 2023,13, 3688-3693

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Small change for big improvement in the preparation of the key intermediate N¹, N³-disubstituted 1,3,5-triazone of ensitrelvir

W. Hu, Y. Liu, X. Zhang, P. Zheng, F. Yang, G. Guo, X. Xie, J. Huang and W. Chen, RSC Adv., 2023, 13, 3688 DOI: 10.1039/D2RA07844A

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