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

• 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: Etravirine; Microwave-promoted; Amination; Synthesis
• Online Access: http://link.springer.com/article/10.1186/s13065-018-0504-4

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.