Synthesis of [$^2$H$_5$]baricitinib via [$^2$H$_5$]ethanesulfonyl chloride

Jansen-van Vuuren, Ross D. (author), Vohra, Rahul (author)

Baricitinib, typically applied as a treatment for rheumatoid arthritis, has recently attracted the attention of clinicians and researchers as a potential treatment for COVID-19. Naturally, there has been a need for the preparation of the isotope-labelled analogue of baricitinib to probe the pharmacokinetics of baricitinib in this new role. As such, we have developed a simple synthetic route to deuterated [$^2$H$_5$]baricitinib, facilitating its formation over four steps and in a 29% overall yield based on starting [$^2$H$_5$]ethanethiol (19% if we start with [$^2$H$_5$]bromoethane instead). A critical component of the overall process involves the synthesis of [$^2$H$_5$]ethanesulfonyl chloride, and we describe in detail the two routes that were explored to optimize this step.

• Language: English
• Keywords: baricitinib, COVID-19, deuteration, deuterium-labelled, SARS-CoV-2, isotopologue
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2022
• Number of pages: Str. 156-161
• Numbering: Vol. 65, iss. 6
• PID: 20.500.12556/RUL-136998
• UDC: 547.1.057:615
• ISSN on article: 1099-1344
• DOI: 10.1002/jlcr.3969
• COBISS.SI-ID: 101564163
• Publication date in RUL: 27.05.2022

Record is a part of a journal

• Title: Journal of labelled compounds & radiopharmaceuticals
• Shortened title: J. labelled compd. radiopharm.
• Publisher: Wiley
• ISSN: 1099-1344
• COBISS.SI-ID: 517762329

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: baricitinib, COVID-19, devteracija, označevanje z devterijem, SARS-CoV-2, izotopolog

Projects

• Funder: Other - Other funder or multiple funders
• Funding programme: Queen's University, COVID-19 Rapid-Response