Products Cited in Publications Worldwide Synthesis of [2H5]baricitinib via [2H5]ethanesulfonyl chloride

Synthesis of [2H5]baricitinib via [2H5]ethanesulfonyl chloride

Jansen-van Vuuren, Ross D.; Vohra, Rahul

DOI: PMID:

Abstract

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-labeled analog of baricitinib to probe the pharmacokinetics of baricitinib in this new role. As such, we have developed a simple synthetic route to deuterated [2H5]baricitinib, facilitating its formation over four steps and in a 29% overall yield based on starting [2H5]ethanethiol (19% if we start with [2H5]bromoethane instead). A critical component of the overall process involves the synthesis of [2H5]ethanesulfonyl chloride, and we describe in detail the two routes that were explored to optimize this step.

Keywords

baricitinib ; COVID-19 ; deuteration ; deuterium-labelled ; isotopologue ; SARS-CoV-2

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