A novel strategy for the manufacture of idelalisib: controlling the formation of an enantiomerElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ra00407b
A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1 S )-1-(9 H -purin-6-ylamino)propyl]-4(3 H )-quinazolinone, idelalisib 1 , has been developed. This strategy controls the desfluoro impurity of 13 during reduction of nitro intermediate 4 , and also arrests the formation of the enantiomer duri...
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| creator | Mekala, Nagaraju Buddepu, Srinivasa Rao Dehury, Sanjay K Moturu, Krishna Murthy V. R Indukuri, Sunil Kumar V Vasireddi, Umamaheswara Rao Parimi, Atchuta R |
| description | A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed. This strategy controls the desfluoro impurity of
13
during reduction of nitro intermediate
4
, and also arrests the formation of the enantiomer during cyclisation of diamide
17
, without affecting the neighbouring chiral centre. This process is demonstrated on a larger scale in the laboratory and achieved good chemical and chiral purities coupled with good yields.
A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed. |
| doi_str_mv | 10.1039/c8ra00407b |
| format | Article |
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S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed. This strategy controls the desfluoro impurity of
13
during reduction of nitro intermediate
4
, and also arrests the formation of the enantiomer during cyclisation of diamide
17
, without affecting the neighbouring chiral centre. This process is demonstrated on a larger scale in the laboratory and achieved good chemical and chiral purities coupled with good yields.
A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed.</description><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c8ra00407b</identifier><creationdate>2018-04</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,864,27924,27925</link.rule.ids></links><search><creatorcontrib>Mekala, Nagaraju</creatorcontrib><creatorcontrib>Buddepu, Srinivasa Rao</creatorcontrib><creatorcontrib>Dehury, Sanjay K</creatorcontrib><creatorcontrib>Moturu, Krishna Murthy V. R</creatorcontrib><creatorcontrib>Indukuri, Sunil Kumar V</creatorcontrib><creatorcontrib>Vasireddi, Umamaheswara Rao</creatorcontrib><creatorcontrib>Parimi, Atchuta R</creatorcontrib><title>A novel strategy for the manufacture of idelalisib: controlling the formation of an enantiomerElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ra00407b</title><description>A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed. This strategy controls the desfluoro impurity of
13
during reduction of nitro intermediate
4
, and also arrests the formation of the enantiomer during cyclisation of diamide
17
, without affecting the neighbouring chiral centre. This process is demonstrated on a larger scale in the laboratory and achieved good chemical and chiral purities coupled with good yields.
A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed.</description><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFj7FKA0EQhpeAYNA09sKUWiTuXeJp0ok5MZVF7MPcOhc3zM4eu3uBPJWvmFWEFBZO8zP83zcwSl0VelLo6fzOPAbUeqYfmoEalnpWjUtdzc_VKMadzlPdF2VVDNXXE4jfE0NMARNtD9D6AOmTwKH0LZrUBwLfgv0gRrbRNgswXlLwzFa2P2hWHCbr5RtEARKUvDoKNZPJqFgDse86JkeSMBzAykm6qderW8A9WsaGaQJrIli-rRbw95tLddYiRxr95oW6fqnfn1_HIZpNF6zLxzcnfPpffwSoYGAV</recordid><startdate>20180427</startdate><enddate>20180427</enddate><creator>Mekala, Nagaraju</creator><creator>Buddepu, Srinivasa Rao</creator><creator>Dehury, Sanjay K</creator><creator>Moturu, Krishna Murthy V. R</creator><creator>Indukuri, Sunil Kumar V</creator><creator>Vasireddi, Umamaheswara Rao</creator><creator>Parimi, Atchuta R</creator><scope/></search><sort><creationdate>20180427</creationdate><title>A novel strategy for the manufacture of idelalisib: controlling the formation of an enantiomerElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ra00407b</title><author>Mekala, Nagaraju ; Buddepu, Srinivasa Rao ; Dehury, Sanjay K ; Moturu, Krishna Murthy V. R ; Indukuri, Sunil Kumar V ; Vasireddi, Umamaheswara Rao ; Parimi, Atchuta R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c8ra00407b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mekala, Nagaraju</creatorcontrib><creatorcontrib>Buddepu, Srinivasa Rao</creatorcontrib><creatorcontrib>Dehury, Sanjay K</creatorcontrib><creatorcontrib>Moturu, Krishna Murthy V. R</creatorcontrib><creatorcontrib>Indukuri, Sunil Kumar V</creatorcontrib><creatorcontrib>Vasireddi, Umamaheswara Rao</creatorcontrib><creatorcontrib>Parimi, Atchuta R</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mekala, Nagaraju</au><au>Buddepu, Srinivasa Rao</au><au>Dehury, Sanjay K</au><au>Moturu, Krishna Murthy V. R</au><au>Indukuri, Sunil Kumar V</au><au>Vasireddi, Umamaheswara Rao</au><au>Parimi, Atchuta R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A novel strategy for the manufacture of idelalisib: controlling the formation of an enantiomerElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ra00407b</atitle><date>2018-04-27</date><risdate>2018</risdate><volume>8</volume><issue>28</issue><spage>15863</spage><epage>15869</epage><pages>15863-15869</pages><eissn>2046-2069</eissn><abstract>A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed. This strategy controls the desfluoro impurity of
13
during reduction of nitro intermediate
4
, and also arrests the formation of the enantiomer during cyclisation of diamide
17
, without affecting the neighbouring chiral centre. This process is demonstrated on a larger scale in the laboratory and achieved good chemical and chiral purities coupled with good yields.
A novel and scalable synthesis of 5-fluoro-3-phenyl-2-[(1
S
)-1-(9
H
-purin-6-ylamino)propyl]-4(3
H
)-quinazolinone, idelalisib
1
, has been developed.</abstract><doi>10.1039/c8ra00407b</doi><tpages>7</tpages></addata></record> |
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| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| title | A novel strategy for the manufacture of idelalisib: controlling the formation of an enantiomerElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ra00407b |
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