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

Pyrrolotriazine 1 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...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-10, Vol.22 (19), p.7656-7661
Main Authors: Paymode, Dinesh J, Cardoso, Flavio S. P, Agrawal, Toolika, Tomlin, John W, Cook, Daniel W, Burns, Justina M, Stringham, Rodger W, Sieber, Joshua D, Gupton, B. Frank, Snead, David R
Format: Article
Language:English
Subjects:
Letter
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13
cites cdi_FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13
container_end_page 7661
container_issue 19
container_start_page 7656
container_title Organic letters
container_volume 22
creator Paymode, Dinesh J
Cardoso, Flavio S. P
Agrawal, Toolika
Tomlin, John W
Cook, Daniel W
Burns, Justina M
Stringham, Rodger W
Sieber, Joshua D
Gupton, B. Frank
Snead, David R
description Pyrrolotriazine 1 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.
doi_str_mv 10.1021/acs.orglett.0c02848
format article
fullrecord <record><control><sourceid>acs_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7536717</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>b496133650</sourcerecordid><originalsourceid>FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13</originalsourceid><addsrcrecordid>eNp9kN1KAzEQhYMotlafQJC8wLb52V8vhFKqFgqK1euQZpM2ZXezJNvF9elNaV30xqsZZs45M3wA3GI0xojgCRdubOymkE0zRgKRNEzPwBBHhAYJish538doAK6c2yGE_SS7BANKMopJGg-BmH_WvMp1tYFTIaRzsDHwTZa5dLrVFraaQ17BRVlb08ocvnbWmsI0VvMvXUm46qpm67XuHq72dV10cCarRlov7VfX4ELxwsmbUx2Bj8f5--w5WL48LWbTZcDDMGoCnEmEw0SlnOJEoljlwlceKykElaFKVIbiNF7LOCeK5ISqNUZKIJoTwTOO6Qg8HHPr_bqUufCPWF6w2uqS244ZrtnfTaW3bGNalkQ0TnDiA-gxQFjjnJWq92LEDsyZZ85OzNmJuXfd_T7be34ge8HkKDi4d2ZvK0_h38hvF76VDg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Paymode, Dinesh J ; Cardoso, Flavio S. P ; Agrawal, Toolika ; Tomlin, John W ; Cook, Daniel W ; Burns, Justina M ; Stringham, Rodger W ; Sieber, Joshua D ; Gupton, B. Frank ; Snead, David R</creator><creatorcontrib>Paymode, Dinesh J ; Cardoso, Flavio S. P ; Agrawal, Toolika ; Tomlin, John W ; Cook, Daniel W ; Burns, Justina M ; Stringham, Rodger W ; Sieber, Joshua D ; Gupton, B. Frank ; Snead, David R</creatorcontrib><description>Pyrrolotriazine 1 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.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.0c02848</identifier><identifier>PMID: 32931286</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Letter</subject><ispartof>Organic letters, 2020-10, Vol.22 (19), p.7656-7661</ispartof><rights>2020 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13</citedby><cites>FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13</cites><orcidid>0000-0001-6607-5097 ; 0000-0003-0621-3624 ; 0000-0002-8608-5054 ; 0000-0003-1239-533X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32931286$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Paymode, Dinesh J</creatorcontrib><creatorcontrib>Cardoso, Flavio S. P</creatorcontrib><creatorcontrib>Agrawal, Toolika</creatorcontrib><creatorcontrib>Tomlin, John W</creatorcontrib><creatorcontrib>Cook, Daniel W</creatorcontrib><creatorcontrib>Burns, Justina M</creatorcontrib><creatorcontrib>Stringham, Rodger W</creatorcontrib><creatorcontrib>Sieber, Joshua D</creatorcontrib><creatorcontrib>Gupton, B. Frank</creatorcontrib><creatorcontrib>Snead, David R</creatorcontrib><title>Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Pyrrolotriazine 1 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.</description><subject>Letter</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kN1KAzEQhYMotlafQJC8wLb52V8vhFKqFgqK1euQZpM2ZXezJNvF9elNaV30xqsZZs45M3wA3GI0xojgCRdubOymkE0zRgKRNEzPwBBHhAYJish538doAK6c2yGE_SS7BANKMopJGg-BmH_WvMp1tYFTIaRzsDHwTZa5dLrVFraaQ17BRVlb08ocvnbWmsI0VvMvXUm46qpm67XuHq72dV10cCarRlov7VfX4ELxwsmbUx2Bj8f5--w5WL48LWbTZcDDMGoCnEmEw0SlnOJEoljlwlceKykElaFKVIbiNF7LOCeK5ISqNUZKIJoTwTOO6Qg8HHPr_bqUufCPWF6w2uqS244ZrtnfTaW3bGNalkQ0TnDiA-gxQFjjnJWq92LEDsyZZ85OzNmJuXfd_T7be34ge8HkKDi4d2ZvK0_h38hvF76VDg</recordid><startdate>20201002</startdate><enddate>20201002</enddate><creator>Paymode, Dinesh J</creator><creator>Cardoso, Flavio S. P</creator><creator>Agrawal, Toolika</creator><creator>Tomlin, John W</creator><creator>Cook, Daniel W</creator><creator>Burns, Justina M</creator><creator>Stringham, Rodger W</creator><creator>Sieber, Joshua D</creator><creator>Gupton, B. Frank</creator><creator>Snead, David R</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6607-5097</orcidid><orcidid>https://orcid.org/0000-0003-0621-3624</orcidid><orcidid>https://orcid.org/0000-0002-8608-5054</orcidid><orcidid>https://orcid.org/0000-0003-1239-533X</orcidid></search><sort><creationdate>20201002</creationdate><title>Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis</title><author>Paymode, Dinesh J ; Cardoso, Flavio S. P ; Agrawal, Toolika ; Tomlin, John W ; Cook, Daniel W ; Burns, Justina M ; Stringham, Rodger W ; Sieber, Joshua D ; Gupton, B. Frank ; Snead, David R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Paymode, Dinesh J</creatorcontrib><creatorcontrib>Cardoso, Flavio S. P</creatorcontrib><creatorcontrib>Agrawal, Toolika</creatorcontrib><creatorcontrib>Tomlin, John W</creatorcontrib><creatorcontrib>Cook, Daniel W</creatorcontrib><creatorcontrib>Burns, Justina M</creatorcontrib><creatorcontrib>Stringham, Rodger W</creatorcontrib><creatorcontrib>Sieber, Joshua D</creatorcontrib><creatorcontrib>Gupton, B. Frank</creatorcontrib><creatorcontrib>Snead, David R</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Paymode, Dinesh J</au><au>Cardoso, Flavio S. P</au><au>Agrawal, Toolika</au><au>Tomlin, John W</au><au>Cook, Daniel W</au><au>Burns, Justina M</au><au>Stringham, Rodger W</au><au>Sieber, Joshua D</au><au>Gupton, B. Frank</au><au>Snead, David R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2020-10-02</date><risdate>2020</risdate><volume>22</volume><issue>19</issue><spage>7656</spage><epage>7661</epage><pages>7656-7661</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Pyrrolotriazine 1 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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>32931286</pmid><doi>10.1021/acs.orglett.0c02848</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-6607-5097</orcidid><orcidid>https://orcid.org/0000-0003-0621-3624</orcidid><orcidid>https://orcid.org/0000-0002-8608-5054</orcidid><orcidid>https://orcid.org/0000-0003-1239-533X</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-10, Vol.22 (19), p.7656-7661
issn 1523-7060
1523-7052
language eng
recordid cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_7536717
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Letter
title Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T19%3A47%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Expanding%20Access%20to%20Remdesivir%20via%20an%20Improved%20Pyrrolotriazine%20Synthesis:%20Supply%20Centered%20Synthesis&rft.jtitle=Organic%20letters&rft.au=Paymode,%20Dinesh%20J&rft.date=2020-10-02&rft.volume=22&rft.issue=19&rft.spage=7656&rft.epage=7661&rft.pages=7656-7661&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.0c02848&rft_dat=%3Cacs_pubme%3Eb496133650%3C/acs_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a445t-19e0147f8a317e06fdc17ea6fecc3e4f7f90686be6d2f2d23fb10fc03d2ca9a13%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/32931286&rfr_iscdi=true