PROCESS FOR THE SYNTHESIS OF BENZYLIDENE ROSIGLITAZONE BASE
Process for the synthesis of 5-{4-[N-methyl-N-(2-pyridyl)-amino-ethoxy]-benzylidene}-thiazolidine-2,4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained...
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creator | UBERHARDT TAMASNE DOBAY LASZLO WERKNE PAPP EVA DEUTSCHNE JUHASZ IDA SEBOK FERENC CZIBULA LASZLO NAGYNE BAGDY JUDIT |
description | Process for the synthesis of 5-{4-[N-methyl-N-(2-pyridyl)-amino-ethoxy]-benzylidene}-thiazolidine-2,4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained compound of formula (III) with 4-fluorobenzaldehyde Step c) reaction of the obtained compound of formula (IV) with thiazolidine-2,4-dione characterized by dissolving 4-{2-[N-methyl-N-(2-pyridyl)amino]-ethanol of formula (III) obtained in Step a) in toluene and using it in Step b) without isolation; reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50° C.; reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product. |
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reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50° C.; reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product.</description><language>eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>2009</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20091029&DB=EPODOC&CC=US&NR=2009270630A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76290</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20091029&DB=EPODOC&CC=US&NR=2009270630A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>UBERHARDT TAMASNE</creatorcontrib><creatorcontrib>DOBAY LASZLO</creatorcontrib><creatorcontrib>WERKNE PAPP EVA</creatorcontrib><creatorcontrib>DEUTSCHNE JUHASZ IDA</creatorcontrib><creatorcontrib>SEBOK FERENC</creatorcontrib><creatorcontrib>CZIBULA LASZLO</creatorcontrib><creatorcontrib>NAGYNE BAGDY JUDIT</creatorcontrib><title>PROCESS FOR THE SYNTHESIS OF BENZYLIDENE ROSIGLITAZONE BASE</title><description>Process for the synthesis of 5-{4-[N-methyl-N-(2-pyridyl)-amino-ethoxy]-benzylidene}-thiazolidine-2,4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained compound of formula (III) with 4-fluorobenzaldehyde Step c) reaction of the obtained compound of formula (IV) with thiazolidine-2,4-dione characterized by dissolving 4-{2-[N-methyl-N-(2-pyridyl)amino]-ethanol of formula (III) obtained in Step a) in toluene and using it in Step b) without isolation; reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50° C.; reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2009</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZLAOCPJ3dg0OVnDzD1II8XBVCI70A1LBnsEK_m4KTq5-UZE-ni6ufq4KQf7Bnu4-niGOUf5AnpNjsCsPA2taYk5xKi-U5mZQdnMNcfbQTS3Ij08tLkhMTs1LLYkPDTYyMLA0MjcwMzZwNDQmThUAoOcqdA</recordid><startdate>20091029</startdate><enddate>20091029</enddate><creator>UBERHARDT TAMASNE</creator><creator>DOBAY LASZLO</creator><creator>WERKNE PAPP EVA</creator><creator>DEUTSCHNE JUHASZ IDA</creator><creator>SEBOK FERENC</creator><creator>CZIBULA LASZLO</creator><creator>NAGYNE BAGDY JUDIT</creator><scope>EVB</scope></search><sort><creationdate>20091029</creationdate><title>PROCESS FOR THE SYNTHESIS OF BENZYLIDENE ROSIGLITAZONE BASE</title><author>UBERHARDT TAMASNE ; DOBAY LASZLO ; WERKNE PAPP EVA ; DEUTSCHNE JUHASZ IDA ; SEBOK FERENC ; CZIBULA LASZLO ; NAGYNE BAGDY JUDIT</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US2009270630A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2009</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>UBERHARDT TAMASNE</creatorcontrib><creatorcontrib>DOBAY LASZLO</creatorcontrib><creatorcontrib>WERKNE PAPP EVA</creatorcontrib><creatorcontrib>DEUTSCHNE JUHASZ IDA</creatorcontrib><creatorcontrib>SEBOK FERENC</creatorcontrib><creatorcontrib>CZIBULA LASZLO</creatorcontrib><creatorcontrib>NAGYNE BAGDY JUDIT</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>UBERHARDT TAMASNE</au><au>DOBAY LASZLO</au><au>WERKNE PAPP EVA</au><au>DEUTSCHNE JUHASZ IDA</au><au>SEBOK FERENC</au><au>CZIBULA LASZLO</au><au>NAGYNE BAGDY JUDIT</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>PROCESS FOR THE SYNTHESIS OF BENZYLIDENE ROSIGLITAZONE BASE</title><date>2009-10-29</date><risdate>2009</risdate><abstract>Process for the synthesis of 5-{4-[N-methyl-N-(2-pyridyl)-amino-ethoxy]-benzylidene}-thiazolidine-2,4-dione (INN name: benzylidene-rosiglitazone) of formula (I), which consist of the following steps: Step a) reaction of 2-chloro-pyridine and 2-(N-methylamino)-ethanol Step b) reaction of the obtained compound of formula (III) with 4-fluorobenzaldehyde Step c) reaction of the obtained compound of formula (IV) with thiazolidine-2,4-dione characterized by dissolving 4-{2-[N-methyl-N-(2-pyridyl)amino]-ethanol of formula (III) obtained in Step a) in toluene and using it in Step b) without isolation; reacting the solution of compound of formula (III) in toluene in Step b) with 4-fluorobenzaldehyde in the presence of aqueous alkali hydroxide solution and phase transfer catalyst at 25-50° C.; reacting the solution of the benzaldehyde derivative of formula (IV) obtained in Step b) in toluene in Step c) and isolating the desired product.</abstract><oa>free_for_read</oa></addata></record> |
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title | PROCESS FOR THE SYNTHESIS OF BENZYLIDENE ROSIGLITAZONE BASE |
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