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Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis

Dinesh J. Paymode, Flávio S. P. Cardoso, Toolika Agrawal, John W. Tomlin, Daniel W. Cook, Justina M. Burns, Rodger W. Stringham, Joshua D. Sieber, B. Frank Gupton, David R. Snead

2020Organic Letters39 citationsDOIOpen Access PDF

Abstract

is an important precursor to remdesivir. Initial results toward an efficient synthesis are disclosed consisting of sequential cyanation, amination, and triazine formation beginning from pyrrole. This route makes use of highly abundant, commoditized raw material inputs. The yield of triazine was doubled from 31% to 59%, and the synthetic step count was reduced from 4 to 2. These efforts help to secure the remdesivir supply chain.

Topics & Concepts

CyanationChemistryYield (engineering)AminationCombinatorial chemistryReductive amination1,3,5-TriazineOrganic chemistryCatalysisMaterials scienceMetallurgyClick Chemistry and ApplicationsSynthesis and Biological EvaluationChemical Reaction Mechanisms
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