Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine

Ashley R. Longstreet, Suzanne M. Opalka, Brian S. Campbell, B. Frank Gupton and D. Tyler McQuade
Beilstein J. Org. Chem. 2013, 9, 2570–2578. https://doi.org/10.3762/bjoc.9.292

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Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine
Ashley R. Longstreet, Suzanne M. Opalka, Brian S. Campbell, B. Frank Gupton and D. Tyler McQuade
Beilstein J. Org. Chem. 2013, 9, 2570–2578. https://doi.org/10.3762/bjoc.9.292

How to Cite

Longstreet, A. R.; Opalka, S. M.; Campbell, B. S.; Gupton, B. F.; McQuade, D. T. Beilstein J. Org. Chem. 2013, 9, 2570–2578. doi:10.3762/bjoc.9.292

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Patents

  • MCQUADE D TYLER; GUPTON FRANK B; LONGSTREET ASHLEY R; OPALKA SUZANNE M. Methods of making 2-halonicotinonitriles. US 9951020 B2, April 24, 2018.
  • MCQUADE D TYLER; GUPTON B FRANK; LONGSTREET ASHLEY R; OPALKA SUZANNE M. METHODS OF MAKING 2-HALONICOTINONITRILES. EP 3043646 A4, May 17, 2017.
  • MCQUADE D TYLER; GUPTON B FRANK; LONGSTREET ASHLEY R; OPALKA SUZANNE M. Methods of making 2-halonicotinonitriles. CN 106061258 A, Oct 26, 2016.
  • AHMAD SAEED; GUPTON FRANK; VERGHESES JENSON; MCQUADE TYLER. LOWCOST, HIGH YIELD SYNTHESIS OF NEVIRAPINE. WO 2016118586 A1, July 28, 2016.
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