Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir

In this study, the key intermediate N(1), N(3)-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...

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Autores principales: Hu, Wei, Liu, Yuanchang, Zhang, Xiang, Zheng, Panpan, Yang, Feifei, Guo, Guangyang, Xie, Xin, Huang, Jiuzhong, Chen, Weiming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890673/
https://www.ncbi.nlm.nih.gov/pubmed/36756552
http://dx.doi.org/10.1039/d2ra07844a
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author Hu, Wei
Liu, Yuanchang
Zhang, Xiang
Zheng, Panpan
Yang, Feifei
Guo, Guangyang
Xie, Xin
Huang, Jiuzhong
Chen, Weiming
author_facet Hu, Wei
Liu, Yuanchang
Zhang, Xiang
Zheng, Panpan
Yang, Feifei
Guo, Guangyang
Xie, Xin
Huang, Jiuzhong
Chen, Weiming
author_sort Hu, Wei
collection PubMed
description In this study, the key intermediate N(1), N(3)-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 N(1)-alkylation. The strategy with simple conditions and operations had a total yield of 53% on a gram scale. The strategy for synthesizing the key N(1), N(3)-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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spelling pubmed-98906732023-02-07 Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir Hu, Wei Liu, Yuanchang Zhang, Xiang Zheng, Panpan Yang, Feifei Guo, Guangyang Xie, Xin Huang, Jiuzhong Chen, Weiming RSC Adv Chemistry In this study, the key intermediate N(1), N(3)-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 N(1)-alkylation. The strategy with simple conditions and operations had a total yield of 53% on a gram scale. The strategy for synthesizing the key N(1), N(3)-disubstituted 1,3,5-triazone intermediate of ensitrelvir might provide a new avenue for further research and development of ensitrelvir analogs. The Royal Society of Chemistry 2023-01-25 /pmc/articles/PMC9890673/ /pubmed/36756552 http://dx.doi.org/10.1039/d2ra07844a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Hu, Wei
Liu, Yuanchang
Zhang, Xiang
Zheng, Panpan
Yang, Feifei
Guo, Guangyang
Xie, Xin
Huang, Jiuzhong
Chen, Weiming
Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title_full Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title_fullStr Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title_full_unstemmed Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title_short Small change for big improvement in the preparation of the key intermediate N(1), N(3)-disubstituted 1,3,5-triazone of ensitrelvir
title_sort small change for big improvement in the preparation of the key intermediate n(1), n(3)-disubstituted 1,3,5-triazone of ensitrelvir
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890673/
https://www.ncbi.nlm.nih.gov/pubmed/36756552
http://dx.doi.org/10.1039/d2ra07844a
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