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ChemicalBook CAS DataBase List 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
500287-72-9

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile synthesis

5synthesis methods
Rilpivirine is a pharmaceutical drug, developed by Tibotec, for the treatment of HIV infection. It is a second-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with higher potency, longer half-life and reduced side-effect profile compared with older NNRTIs, such as efavirenz. Rilpivirine entered phase III clinical trials in April 2008, and was approved for use in the United States in May 2011. A fixed-dose drug combining rilpivirine with emtricitabine and tenofovir, was approved by the U.S. Food and Drug Administration in August 2011 under the brand name Complera.
Synthetic Routes
  • ROUTE 1

    • 202112071640540295.jpg

    Guillemont, Jerome; Pasquier, Elisabeth; Palandjian, Patrice; Vernier, Daniel; Gaurrand, Sandrine; Lewi, Paul J.; Heeres, Jan; de Jonge, Marc R.; Koymans, Lucien M. H.; Daeyaert, Frits F. D.; Vinkers, Maarten H.; Arnold, Edward; Das, Kalyan; Pauwels, Rudi; Andries, Koen; de Bethune, Marie-Pierre; Bettens, Eva; Hertogs, Kurt; Wigerinck, Piet; Timmerman, Philip; Janssen, Paul A. J. Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1. Journal of Medicinal Chemistry. Volume 48. Issue 6. Pages 2072-2079. Journal. (2005).

  • ROUTE 2

    • 202112071148294790.jpg

    Bollini, Mariela; Cisneros, Jose A.; Spasov, Krasimir A.; Anderson, Karen S.; Jorgensen, William L. Optimization of diarylazines as anti-?HIV agents with dramatically enhanced solubility. Bioorganic & Medicinal Chemistry Letters. Volume 23. Issue 18. Pages 5213-5216. Journal; Online Computer File. (2013).

  • ROUTE 3

    • 202112076089028792.jpg

    Srinivasan, Thirumalai Rajan; Sajja, Eswaraiah; Venkatesh, Mummadi. A process for the preparation of rilpivirine hydrochloride. Assignee?MSN Laboratories Limited, India. IN?2012CH05368. (2015).

  • ROUTE 4

    • 202112078323238392.jpg

    Reddy, Bandi Parthasaradhi; Reddy, Kura Rathnakar; Reddy, Dasari Muralidhara; Reddy, Adulla Venkat Narsimha; Krishna, Bandi Vamsi. Process for rilpivirine. Assignee?Hetero Research Foundation, India. (2012).

  • ROUTE 5

    • 202112070383765505.jpg

    Gurjar, Mukund Keshav; Maikap, Golakchandra Sudarshan; Joshi, Shashikant Gangaram; Badhe, Sachin Aravind; Mehta, Samit Satish. An improved process of preparing rilpivirine. Assignee?Emcure Pharmaceuticals Limited, India. IN?2011MU01223. (2012).

  • ROUTE 6

    • 202112074403070348.jpg

    Li, Jinliang; Cai, Zhigang; Shao, Lanying; Zhou, Xiajun. Process for preparation of rilpivirine and intermediates thereof. Assignee?Shanghai Desano Pharmaceutical Co., Ltd., Peop. Rep. China; Shanghai Desano Chemical Pharmaceutical Co., Ltd. CN?103183642. (2013).

  • ROUTE 7

    • 202112071657221256.jpg

    Li, Jinliang; Cai, Zhigang; Shao, Lanying; Zhou, Xiajun. Process for preparation of rilpivirine and intermediates thereof. Assignee?Shanghai Desano Pharmaceutical Co., Ltd., Peop. Rep. China; Shanghai Desano Chemical Pharmaceutical Co., Ltd. CN?103183641. (2013).

  • ROUTE 8

    • 202112070044135491.jpg

    Vandecruys, Roger Petrus Gerebern. Pharmaceutical compositions comprising a surfactant and a physiologically tolerable water-soluble acid respectively base, and a basic respectively acidic drug compound, containing a pyrimidine unit, for treating HIV. Assignee?Janssen Pharmaceutica N.V., Belg. WO?2004050068. (2004).

202112071640540295.jpg

Guillemont, Jerome; Pasquier, Elisabeth; Palandjian, Patrice; Vernier, Daniel; Gaurrand, Sandrine; Lewi, Paul J.; Heeres, Jan; de Jonge, Marc R.; Koymans, Lucien M. H.; Daeyaert, Frits F. D.; Vinkers, Maarten H.; Arnold, Edward; Das, Kalyan; Pauwels, Rudi; Andries, Koen; de Bethune, Marie-Pierre; Bettens, Eva; Hertogs, Kurt; Wigerinck, Piet; Timmerman, Philip; Janssen, Paul A. J. Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1. Journal of Medicinal Chemistry. Volume 48. Issue 6. Pages 2072-2079. Journal. (2005).

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Yield:500287-72-9 93.9%

Reaction Conditions:

with trichlorophosphate at 20;Reflux;

Steps:

3 Synthesis of compound V:

Add compound VI (10.00g, 26.0mmoL) and 80ml phosphorous oxychloride as solvent in a 500mL three-necked flask. Stir for 2-3h at 20-30, then heat to reflux for 3h. TLC tracked until the compound VI remained unchanged, the temperature was lowered to 5-10°C, the stirring was continued for 1 h, and then suction filtered and dried to obtain 9.05 g of a light yellow solid, which was the crude compound V, with a yield of 95.0%. Add all the above-mentioned light yellow solids into a 500ml three-necked flask containing 300ml of acetone, heat it to clear, and then add 0.8g of activated carbon. Incubate and stir for 1 hour. After filtering while hot, the filtrate is spin-dried to obtain 8.50 g of a white solid, which is a pure product of compound V, with a purity of 99.74% and a yield of 93.9%.

References:

CN112010810,2020,A Location in patent:Paragraph 0034; 0067-0070

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