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[2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis
1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472761/ https://www.ncbi.nlm.nih.gov/pubmed/32939297 http://dx.doi.org/10.1107/S2056989020010658 |
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author | Eckhardt, Tamira Goddard, Richard Rudolph, Ines Richter, Adrian Lehmann, Christoph Imming, Peter Seidel, Rüdiger W. |
author_facet | Eckhardt, Tamira Goddard, Richard Rudolph, Ines Richter, Adrian Lehmann, Christoph Imming, Peter Seidel, Rüdiger W. |
author_sort | Eckhardt, Tamira |
collection | PubMed |
description | 1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(trifluoromethyl)-1,3-benzothiazin-4-one, following the original synthetic route, whereby the corresponding benzoyl isothiocyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The trifluoromethyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for intermolecular weak C—H⋯O hydrogen bonds. |
format | Online Article Text |
id | pubmed-7472761 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-74727612020-09-15 [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis Eckhardt, Tamira Goddard, Richard Rudolph, Ines Richter, Adrian Lehmann, Christoph Imming, Peter Seidel, Rüdiger W. Acta Crystallogr E Crystallogr Commun Research Communications 1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C(13)H(12)ClF(3)N(2)O(3), occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(trifluoromethyl)-1,3-benzothiazin-4-one, following the original synthetic route, whereby the corresponding benzoyl isothiocyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The trifluoromethyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for intermolecular weak C—H⋯O hydrogen bonds. International Union of Crystallography 2020-08-11 /pmc/articles/PMC7472761/ /pubmed/32939297 http://dx.doi.org/10.1107/S2056989020010658 Text en © Eckhardt et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Eckhardt, Tamira Goddard, Richard Rudolph, Ines Richter, Adrian Lehmann, Christoph Imming, Peter Seidel, Rüdiger W. [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title | [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title_full | [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title_fullStr | [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title_full_unstemmed | [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title_short | [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
title_sort | [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7472761/ https://www.ncbi.nlm.nih.gov/pubmed/32939297 http://dx.doi.org/10.1107/S2056989020010658 |
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