Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine
2-Chloro-3-amino-4-picoline (CAPIC) is a strategic building block for the preparation of nevirapine, a widely-prescribed non-nucleosidic reverse transcriptase inhibitor for the treatment of HIV-infected patients. A continuous synthesis to the bromo derivative of a CAPIC intermediate, 2-bromo-4-methy...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.292 |
| _version_ | 1819133052688793600 |
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| author | Ashley R. Longstreet Suzanne M. Opalka Brian S. Campbell B. Frank Gupton D. Tyler McQuade |
| author_facet | Ashley R. Longstreet Suzanne M. Opalka Brian S. Campbell B. Frank Gupton D. Tyler McQuade |
| author_sort | Ashley R. Longstreet |
| collection | DOAJ |
| description | 2-Chloro-3-amino-4-picoline (CAPIC) is a strategic building block for the preparation of nevirapine, a widely-prescribed non-nucleosidic reverse transcriptase inhibitor for the treatment of HIV-infected patients. A continuous synthesis to the bromo derivative of a CAPIC intermediate, 2-bromo-4-methylnicotinonitrile, that terminates in a dead-end crystallization is described. The route uses inexpensive, acyclic commodity-based raw materials and has the potential to enable lower cost production of nevirapine as well as other value added structures that contain complex pyridines. The route terminates in a batch crystallization yielding high purity CAPIC. This outcome is expected to facilitate regulatory implementation of the overall process. |
| first_indexed | 2024-12-22T09:41:10Z |
| format | Article |
| id | doaj.art-163f1c80c3374511963b38a2d0baac69 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T09:41:10Z |
| publishDate | 2013-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-163f1c80c3374511963b38a2d0baac692022-12-21T18:30:39ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-11-01912570257810.3762/bjoc.9.2921860-5397-9-292Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapineAshley R. Longstreet0Suzanne M. Opalka1Brian S. Campbell2B. Frank Gupton3D. Tyler McQuade4Department of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, FL 32306, United StatesDepartment of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, FL 32306, United StatesDepartment of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, FL 32306, United StatesDepartment of Chemistry, Virginia Commonwealth University, 1001 West Main Street, P.O. Box 842006 Richmond, Virginia 23284, United StatesDepartment of Chemistry and Biochemistry, Florida State University, 95 Chieftan Way, Tallahassee, FL 32306, United States2-Chloro-3-amino-4-picoline (CAPIC) is a strategic building block for the preparation of nevirapine, a widely-prescribed non-nucleosidic reverse transcriptase inhibitor for the treatment of HIV-infected patients. A continuous synthesis to the bromo derivative of a CAPIC intermediate, 2-bromo-4-methylnicotinonitrile, that terminates in a dead-end crystallization is described. The route uses inexpensive, acyclic commodity-based raw materials and has the potential to enable lower cost production of nevirapine as well as other value added structures that contain complex pyridines. The route terminates in a batch crystallization yielding high purity CAPIC. This outcome is expected to facilitate regulatory implementation of the overall process.https://doi.org/10.3762/bjoc.9.292continuousflow chemistryHIVKnoevenagelnevirapinenicotinonitriles |
| spellingShingle | Ashley R. Longstreet Suzanne M. Opalka Brian S. Campbell B. Frank Gupton D. Tyler McQuade Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine Beilstein Journal of Organic Chemistry continuous flow chemistry HIV Knoevenagel nevirapine nicotinonitriles |
| title | Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| title_full | Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| title_fullStr | Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| title_full_unstemmed | Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| title_short | Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| title_sort | investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine |
| topic | continuous flow chemistry HIV Knoevenagel nevirapine nicotinonitriles |
| url | https://doi.org/10.3762/bjoc.9.292 |
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