Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide

Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide

This invention relates to the novel process for the manufacturing of 3-hydroxy-N,1,6-trialkyl4-oxo-1,4-dihydropyridine-2-carboxamide of formula 1, The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: Th...

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Hauptverfasser: Tam, Tim F, Li, Wanren
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Li, Wanren
description This invention relates to the novel process for the manufacturing of 3-hydroxy-N,1,6-trialkyl4-oxo-1,4-dihydropyridine-2-carboxamide of formula 1, The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.
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Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.</description><language>eng</language><creationdate>2002</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6476229$$EPDF$$P50$$Guspatents$$Hfree_for_read</linktopdf><link.rule.ids>230,308,780,802,885,64039</link.rule.ids><linktorsrc>$$Uhttps://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6476229$$EView_record_in_USPTO$$FView_record_in_$$GUSPTO$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Tam, Tim F</creatorcontrib><creatorcontrib>Li, Wanren</creatorcontrib><creatorcontrib>Apotex, Inc</creatorcontrib><title>Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide</title><description>This invention relates to the novel process for the manufacturing of 3-hydroxy-N,1,6-trialkyl4-oxo-1,4-dihydropyridine-2-carboxamide of formula 1, The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.</description><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2002</creationdate><recordtype>patent</recordtype><sourceid>EFH</sourceid><recordid>eNqNyr0KwjAQAOAuDqK-Qx6gB_aHFmdRnMTBXc7k0gbbXLmk0Ly9KD6A07d860zfhDWFQEFZFhV7UiP62aKOszjfKbaqgj4Z4SXBNS_yBqI4HF5pgBp4YSjyGoz7limJM84TlKBRnrzg6Axts5XFIdDu5yZT59P9eIE5TBjJx_DoBD_sm7ptyvJQ_VHehKA94w</recordid><startdate>20021105</startdate><enddate>20021105</enddate><creator>Tam, Tim F</creator><creator>Li, Wanren</creator><scope>EFH</scope></search><sort><creationdate>20021105</creationdate><title>Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide</title><author>Tam, Tim F ; Li, Wanren</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-uspatents_grants_064762293</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2002</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Tam, Tim F</creatorcontrib><creatorcontrib>Li, Wanren</creatorcontrib><creatorcontrib>Apotex, Inc</creatorcontrib><collection>USPTO Issued Patents</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Tam, Tim F</au><au>Li, Wanren</au><aucorp>Apotex, Inc</aucorp><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide</title><date>2002-11-05</date><risdate>2002</risdate><abstract>This invention relates to the novel process for the manufacturing of 3-hydroxy-N,1,6-trialkyl4-oxo-1,4-dihydropyridine-2-carboxamide of formula 1, The present invention relates to a novel process for the preparation of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I: The method comprises of the TEMPO oxidation of a primary alcohol of 3-O-protected-2-hydroxymethyl-6-alkyl-4H-pyran-4-one of formula III to 3-O-protected-6-alkyl-4-oxo-4H-pyran-2-carboxylic acid of formula II. Reaction of compound of formula II with methylamine and 1,1-carbonyldiimidazole in an inert solvent affords 3-O-protected-N, 1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide, which is deprotected to give of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide of formula I.</abstract><oa>free_for_read</oa></addata></record>
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title Processes for the manufacturing of 3-hydroxy-N,1,6-trialkyl-4-oxo-1,4-dihydropyridine-2-carboxamide
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