Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir

[Image: see text] Pyrrolo[2,1-f][1,2,4]triazine (1) is an important regulatory starting material in the production of the antiviral drug remdesivir. Compound 1 was produced through a newly developed synthetic methodology utilizing simple building blocks such as pyrrole, chloramine, and formamidine a...

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Autores principales: Roy, Sarabindu, Yadaw, Ajay, Roy, Subho, Sirasani, Gopal, Gangu, Aravind, Brown, Jack D., Armstrong, Joseph D., Stringham, Rodger W., Gupton, B. Frank, Senanayake, Chris H., Snead, David R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8787819/
https://www.ncbi.nlm.nih.gov/pubmed/35095258
http://dx.doi.org/10.1021/acs.oprd.1c00071
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author Roy, Sarabindu
Yadaw, Ajay
Roy, Subho
Sirasani, Gopal
Gangu, Aravind
Brown, Jack D.
Armstrong, Joseph D.
Stringham, Rodger W.
Gupton, B. Frank
Senanayake, Chris H.
Snead, David R.
author_facet Roy, Sarabindu
Yadaw, Ajay
Roy, Subho
Sirasani, Gopal
Gangu, Aravind
Brown, Jack D.
Armstrong, Joseph D.
Stringham, Rodger W.
Gupton, B. Frank
Senanayake, Chris H.
Snead, David R.
author_sort Roy, Sarabindu
collection PubMed
description [Image: see text] Pyrrolo[2,1-f][1,2,4]triazine (1) is an important regulatory starting material in the production of the antiviral drug remdesivir. Compound 1 was produced through a newly developed synthetic methodology utilizing simple building blocks such as pyrrole, chloramine, and formamidine acetate by examining the mechanistic pathway for the process optimization exercise. Triazine 1 was obtained in 55% overall yield in a two-vessel-operated process. This work describes the safety of the process, impurity profiles and control, and efforts toward the scale-up of triazine for the preparation of kilogram quantity.
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spelling pubmed-87878192022-01-26 Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir Roy, Sarabindu Yadaw, Ajay Roy, Subho Sirasani, Gopal Gangu, Aravind Brown, Jack D. Armstrong, Joseph D. Stringham, Rodger W. Gupton, B. Frank Senanayake, Chris H. Snead, David R. Org Process Res Dev [Image: see text] Pyrrolo[2,1-f][1,2,4]triazine (1) is an important regulatory starting material in the production of the antiviral drug remdesivir. Compound 1 was produced through a newly developed synthetic methodology utilizing simple building blocks such as pyrrole, chloramine, and formamidine acetate by examining the mechanistic pathway for the process optimization exercise. Triazine 1 was obtained in 55% overall yield in a two-vessel-operated process. This work describes the safety of the process, impurity profiles and control, and efforts toward the scale-up of triazine for the preparation of kilogram quantity. American Chemical Society 2022-01-07 2022-01-21 /pmc/articles/PMC8787819/ /pubmed/35095258 http://dx.doi.org/10.1021/acs.oprd.1c00071 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Roy, Sarabindu
Yadaw, Ajay
Roy, Subho
Sirasani, Gopal
Gangu, Aravind
Brown, Jack D.
Armstrong, Joseph D.
Stringham, Rodger W.
Gupton, B. Frank
Senanayake, Chris H.
Snead, David R.
Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title_full Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title_fullStr Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title_full_unstemmed Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title_short Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir
title_sort facile and scalable methodology for the pyrrolo[2,1-f][1,2,4]triazine of remdesivir
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8787819/
https://www.ncbi.nlm.nih.gov/pubmed/35095258
http://dx.doi.org/10.1021/acs.oprd.1c00071
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