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  1. Article ; Online: Sulfone-Mediated S

    Patel, Nitinchandra D / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A / Yee, Nathan K / Senanayake, Chris H

    The Journal of organic chemistry

    2020  Volume 85, Issue 13, Page(s) 8339–8351

    Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive ... ...

    Abstract An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive S
    MeSH term(s) Antiviral Agents ; Ethers ; Hepacivirus ; Hepatitis C ; Humans ; Protease Inhibitors/pharmacology ; Sulfones ; Viral Nonstructural Proteins
    Chemical Substances Antiviral Agents ; Ethers ; Protease Inhibitors ; Sulfones ; Viral Nonstructural Proteins
    Language English
    Publishing date 2020-06-19
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.0c00554
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More—Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

    Patel, Nitinchandra D. / Wei, Xudong / Byrne, Denis / Narayanan, Bikshandarkoil A. / Pennino, Scott / Sarvestani, Max / Saha, Anjan / Haddad, Nizar / Kapadia, Suresh / Lorenz, Jon C. / DeCroos, Philomen / Ye, Andrew / Lee, Heewon / Grinberg, Nelu / Hossain, Azad / Busacca, Carl A. / Yee, Nathan K. / Senanayake, Chris H.

    Journal of organic chemistry. 2020 May 28, v. 85, no. 13

    2020  

    Abstract: An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high ... ...

    Abstract An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
    Keywords alcohols ; ethers ; journals ; organic chemistry ; proteinase inhibitors
    Language English
    Dates of publication 2020-0528
    Size p. 8339-8351.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.0c00554
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  3. Article: Development of a concise, scalable synthesis of a CCR1 antagonist utilizing a continuous flow Curtius rearrangement

    Marsini, Maurice A / Buono, Frederic G / Lorenz, Jon C / Yang, Bing-Shiou / Reeves, Jonathan T / Sidhu, Kanwar / Sarvestani, Max / Tan, Zhulin / Zhang, Yongda / Li, Ning / Lee, Heewon / Brazzillo, Jason / Nummy, Laurence J / Chung, J. C / Luvaga, Irungu K / Narayanan, Bikshandarkoil A / Wei, Xudong / Song, Jinhua J / Roschangar, Frank /
    Yee, Nathan K / Senanayake, Chris H

    Green chemistry. 2017 Mar. 20, v. 19, no. 6

    2017  

    Abstract: A convergent, robust, and concise synthesis of a developmental CCR1 antagonist is described using continuous flow technology. In the first approach, following an expeditious SNAr sequence for cyclopropane introduction, a safe, continuous flow Curtius ... ...

    Abstract A convergent, robust, and concise synthesis of a developmental CCR1 antagonist is described using continuous flow technology. In the first approach, following an expeditious SNAr sequence for cyclopropane introduction, a safe, continuous flow Curtius rearrangement was developed for the synthesis of a p-methoxybenzyl (PMB) carbamate. Based on kinetic studies, a highly efficient and green process comprising three chemical transformations (azide formation, rearrangement, and isocyanate trapping) was developed with a relatively short residence time and high material throughput (0.8 kg h−1, complete E-factor = ∼9) and was successfully executed on 40 kg scale. Moreover, mechanistic studies enabled the execution of a semi-continuous, tandem Curtius rearrangement and acid–isocyanate coupling to directly afford the final drug candidate in a single, protecting group-free operation. The resulting API synthesis is further determined to be extremely green (RPG = 166%) relative to the industrial average for molecules of similar complexity.
    Keywords CCR1 receptor ; antagonists ; azides ; drugs ; green chemistry
    Language English
    Dates of publication 2017-0320
    Size p. 1454-1461.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ZDB-ID 2006274-6
    ISSN 1463-9270 ; 1463-9262
    ISSN (online) 1463-9270
    ISSN 1463-9262
    DOI 10.1039/c6gc03123d
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  4. Article: Zinc Catalyzed and Mediated Asymmetric Propargylation of Trifluoromethyl Ketones with a Propargyl Boronate

    Fandrick, Daniel R / Reeves Jonathan T / Bakonyi Johanna M / Nyalapatla Prasanth R / Tan Zhulin / Niemeier Oliver / Akalay Deniz / Fandrick Keith R / Wohlleben Wolfgang / Ollenberger Swetlana / Song Jinhua J / Sun Xiufeng / Qu Bo / Haddad Nizar / Sanyal Sanjit / Shen Sherry / Ma Shengli / Byrne Denis / Chitroda Ashish /
    Fuchs Victor / Narayanan Bikshandarkoil A / Grinberg Nelu / Lee Heewon / Yee Nathan / Brenner Michael / Senanayake Chris H

    Journal of organic chemistry. 2013 Apr. 19, v. 78, no. 8

    2013  

    Abstract: The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was ... ...

    Abstract The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was successfully applied on a multikilogram scale for the synthesis of the Glucocorticoid agonist BI 653048. A mechanism for the boron–zinc exchange with a propargyl borolane is proposed and supported by modeling at the density functional level of theory. A water acceleration effect on the zinc-catalyzed propargylation was discovered, which enabled a catalytic process to be achieved. Reaction progress analysis supports a predominately rate limiting exchange for the zinc-catalyzed propargylation. A catalytic amount of water is proposed to generate an intermediate that catalyzes the exchange, thereby facilitating the reaction with trifluoromethyl ketones.
    Keywords agonists ; catalytic activity ; chemical reactions ; chemical structure ; ketones ; ligands ; models ; organic chemistry ; stereoselectivity ; zinc
    Language English
    Dates of publication 2013-0419
    Size p. 3592-3615.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo400080y
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    In stock of ZB MED Bonn / Germany

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  5. Article ; Online: Zinc catalyzed and mediated asymmetric propargylation of trifluoromethyl ketones with a propargyl boronate.

    Fandrick, Daniel R / Reeves, Jonathan T / Bakonyi, Johanna M / Nyalapatla, Prasanth R / Tan, Zhulin / Niemeier, Oliver / Akalay, Deniz / Fandrick, Keith R / Wohlleben, Wolfgang / Ollenberger, Swetlana / Song, Jinhua J / Sun, Xiufeng / Qu, Bo / Haddad, Nizar / Sanyal, Sanjit / Shen, Sherry / Ma, Shengli / Byrne, Denis / Chitroda, Ashish /
    Fuchs, Victor / Narayanan, Bikshandarkoil A / Grinberg, Nelu / Lee, Heewon / Yee, Nathan / Brenner, Michael / Senanayake, Chris H

    The Journal of organic chemistry

    2013  Volume 78, Issue 8, Page(s) 3592–3615

    Abstract: The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was ... ...

    Abstract The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was successfully applied on a multikilogram scale for the synthesis of the Glucocorticoid agonist BI 653048. A mechanism for the boron-zinc exchange with a propargyl borolane is proposed and supported by modeling at the density functional level of theory. A water acceleration effect on the zinc-catalyzed propargylation was discovered, which enabled a catalytic process to be achieved. Reaction progress analysis supports a predominately rate limiting exchange for the zinc-catalyzed propargylation. A catalytic amount of water is proposed to generate an intermediate that catalyzes the exchange, thereby facilitating the reaction with trifluoromethyl ketones.
    MeSH term(s) Boronic Acids/chemistry ; Catalysis ; Hydrocarbons, Fluorinated/chemistry ; Ketones/chemistry ; Molecular Structure ; Pargyline/analogs & derivatives ; Pargyline/chemistry ; Proline/analogs & derivatives ; Proline/chemistry ; Stereoisomerism ; Zinc/chemistry
    Chemical Substances Boronic Acids ; Hydrocarbons, Fluorinated ; Ketones ; Proline (9DLQ4CIU6V) ; Pargyline (9MV14S8G3E) ; Zinc (J41CSQ7QDS)
    Language English
    Publishing date 2013-04-19
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo400080y
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
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  6. Article: Development of a Large Scale Asymmetric Synthesis of the Glucocorticoid Agonist BI 653048 BS H3PO4

    Reeves, Jonathan T / Fandrick Daniel R / Tan Zhulin / Song Jinhua J / Rodriguez Sonia / Qu Bo / Kim Soojin / Niemeier Oliver / Li Zhibin / Byrne Denis / Campbell Scot / Chitroda Ashish / DeCroos Phil / Fachinger Thomas / Fuchs Victor / Gonnella Nina C / Grinberg Nelu / Haddad Nizar / Jäger Burkhard /
    Lee Heewon / Lorenz Jon C / Ma Shengli / Narayanan Bikshandarkoil A / Nummy Larry J / Premasiri Ajith / Roschangar Frank / Sarvestani Max / Shen Sherry / Spinelli Earl / Sun Xiufeng / Varsolona Richard J / Yee Nathan / Brenner Michael / Senanayake Chris H

    Journal of organic chemistry. 2013 Apr. 19, v. 78, no. 8

    2013  

    Abstract: The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H₃PO₄ (1·H₃PO₄) is presented. A key trifluoromethyl ketone intermediate 22 containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine†...

    Abstract The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H₃PO₄ (1·H₃PO₄) is presented. A key trifluoromethyl ketone intermediate 22 containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine–magnesium exchange/electrophile trapping reaction. A nonselective propargylation of trifluoromethyl ketone 22 gave the desired diastereomer in 32% yield and with dr = 98:2 from a 1:1 diastereomeric mixture after crystallization. Subsequently, an asymmetric propargylation was developed which provided the desired diastereomer in 4:1 diastereoselectivity and 75% yield with dr = 99:1 after crystallization. The azaindole moiety was efficiently installed by a one-pot cross coupling/indolization reaction. An efficient deprotection of the 4-methoxyphenethyl group was developed using H₃PO₄/anisole to produce the anisole solvate of the API in high yield and purity. The final form, a phosphoric acid cocrystal, was produced in high yield and purity and with consistent control of particle size.
    Keywords Lewis acids ; agonists ; chemical reactions ; crystallization ; diastereomers ; diastereoselectivity ; moieties ; organic chemistry ; organic compounds ; particle size ; phosphoric acid
    Language English
    Dates of publication 2013-0419
    Size p. 3616-3635.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021%2Fjo400079z
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  7. Article ; Online: Development of a large scale asymmetric synthesis of the glucocorticoid agonist BI 653048 BS H3PO4.

    Reeves, Jonathan T / Fandrick, Daniel R / Tan, Zhulin / Song, Jinhua J / Rodriguez, Sonia / Qu, Bo / Kim, Soojin / Niemeier, Oliver / Li, Zhibin / Byrne, Denis / Campbell, Scot / Chitroda, Ashish / DeCroos, Phil / Fachinger, Thomas / Fuchs, Victor / Gonnella, Nina C / Grinberg, Nelu / Haddad, Nizar / Jäger, Burkhard /
    Lee, Heewon / Lorenz, Jon C / Ma, Shengli / Narayanan, Bikshandarkoil A / Nummy, Larry J / Premasiri, Ajith / Roschangar, Frank / Sarvestani, Max / Shen, Sherry / Spinelli, Earl / Sun, Xiufeng / Varsolona, Richard J / Yee, Nathan / Brenner, Michael / Senanayake, Chris H

    The Journal of organic chemistry

    2013  Volume 78, Issue 8, Page(s) 3616–3635

    Abstract: The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H3PO4 (1·H3PO4) is presented. A key trifluoromethyl ketone intermediate 22 containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine-magnesium ...

    Abstract The development of a large scale synthesis of the glucocorticoid agonist BI 653048 BS H3PO4 (1·H3PO4) is presented. A key trifluoromethyl ketone intermediate 22 containing an N-(4-methoxyphenyl)ethyl amide was prepared by an enolization/bromine-magnesium exchange/electrophile trapping reaction. A nonselective propargylation of trifluoromethyl ketone 22 gave the desired diastereomer in 32% yield and with dr = 98:2 from a 1:1 diastereomeric mixture after crystallization. Subsequently, an asymmetric propargylation was developed which provided the desired diastereomer in 4:1 diastereoselectivity and 75% yield with dr = 99:1 after crystallization. The azaindole moiety was efficiently installed by a one-pot cross coupling/indolization reaction. An efficient deprotection of the 4-methoxyphenethyl group was developed using H3PO4/anisole to produce the anisole solvate of the API in high yield and purity. The final form, a phosphoric acid cocrystal, was produced in high yield and purity and with consistent control of particle size.
    MeSH term(s) Amides/chemistry ; Benzamides/chemistry ; Glucocorticoids/agonists ; Glucocorticoids/chemistry ; Molecular Structure ; Pyridines/chemistry ; Pyrroles/chemistry ; Stereoisomerism
    Chemical Substances Amides ; BI 653048 BS H3PO4 ; Benzamides ; Glucocorticoids ; Pyridines ; Pyrroles
    Language English
    Publishing date 2013-04-19
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo400079z
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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