Development of a practical synthesis of etravirine via a microwave-promoted amination

Abstract Background Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as th...

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Main Authors: Da Feng, Fenju Wei, Zhao Wang, Dongwei Kang, Peng Zhan, Xinyong Liu
Format: Article
Language:English
Published: BMC 2018-12-01
Series:Chemistry Central Journal
Subjects:
Online Access:http://link.springer.com/article/10.1186/s13065-018-0504-4
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author Da Feng
Fenju Wei
Zhao Wang
Dongwei Kang
Peng Zhan
Xinyong Liu
author_facet Da Feng
Fenju Wei
Zhao Wang
Dongwei Kang
Peng Zhan
Xinyong Liu
author_sort Da Feng
collection DOAJ
description Abstract Background Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as the long reaction time and poor yield. Results This article describes our efforts to develop an efficient, practical, microwave-promoted synthetic method for one key intermediate of ETV, which is capable of being operated on a scale-up synthesis level. Through this optimized synthetic procedure, the amination reaction time decreased from 12 h to 15 min and the overall yield improved from 30.4 to 38.5%. Conclusion Overall, we developed a practical synthesis of ETV via a microwave-promoted method, and the synthetic procedure could be amenable to scale-up, and production costs could be significantly lowered.
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spelling doaj.art-c601a3fe13024ce48a5d646168094fbf2022-12-21T22:45:48ZengBMCChemistry Central Journal1752-153X2018-12-011211610.1186/s13065-018-0504-4Development of a practical synthesis of etravirine via a microwave-promoted aminationDa Feng0Fenju Wei1Zhao Wang2Dongwei Kang3Peng Zhan4Xinyong Liu5Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityDepartment of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong UniversityAbstract Background Etravirine (ETV) was approved as the second generation drug for use in individuals infected with HIV-1 in 2008 by the U.S. FDA with its unique antiviral activity, high specificity, and low toxicity. However, there are some shortcomings of the existing synthetic routes, such as the long reaction time and poor yield. Results This article describes our efforts to develop an efficient, practical, microwave-promoted synthetic method for one key intermediate of ETV, which is capable of being operated on a scale-up synthesis level. Through this optimized synthetic procedure, the amination reaction time decreased from 12 h to 15 min and the overall yield improved from 30.4 to 38.5%. Conclusion Overall, we developed a practical synthesis of ETV via a microwave-promoted method, and the synthetic procedure could be amenable to scale-up, and production costs could be significantly lowered.http://link.springer.com/article/10.1186/s13065-018-0504-4EtravirineMicrowave-promotedAminationSynthesis
spellingShingle Da Feng
Fenju Wei
Zhao Wang
Dongwei Kang
Peng Zhan
Xinyong Liu
Development of a practical synthesis of etravirine via a microwave-promoted amination
Chemistry Central Journal
Etravirine
Microwave-promoted
Amination
Synthesis
title Development of a practical synthesis of etravirine via a microwave-promoted amination
title_full Development of a practical synthesis of etravirine via a microwave-promoted amination
title_fullStr Development of a practical synthesis of etravirine via a microwave-promoted amination
title_full_unstemmed Development of a practical synthesis of etravirine via a microwave-promoted amination
title_short Development of a practical synthesis of etravirine via a microwave-promoted amination
title_sort development of a practical synthesis of etravirine via a microwave promoted amination
topic Etravirine
Microwave-promoted
Amination
Synthesis
url http://link.springer.com/article/10.1186/s13065-018-0504-4
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