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ChemicalBook CAS DataBase List Cinacalcet hydrochloride
364782-34-3

Cinacalcet hydrochloride synthesis

8synthesis methods
Cinacalcet Hydrochloride is a type II calcimimetic agent which controls calcium levels in cells by allosteric activation of CaSR. In the presence of calcium ions, it can inhibit parathyroid hormone secretion by activating CaSR in parathyroid glands. Studies show that Cinacalcet Hydrochloride affects cell proliferation in CHO cells transfected with CaSRs. In addition, it is known that Cinacalcet Hydrochloride inhibits the secretion of the parathyroid hormone (PTH). Cinacalcet has been used clinically to treat secondary hyperparathyroidism due to end-stage renal disease or hypercalcemia in patients with parathyroid carcinoma.
Synthetic Routes
  • ROUTE 1

    • 202112077769066218.jpg

    Arava, Veera R.; Gorentla, Laxminarasimhulu; Dubey, Pramod K. A novel asymmetric synthesis of cinacalcet hydrochloride. Beilstein Journal of Organic Chemistry. R&D Laboratory. Suven Life Sciences Ltd. Hyderabad, India. Volume 8. Pages 1366-1373, No. 158. 2012

  • ROUTE 2

    • 202112076590527858.jpg

    Niu, Dawen; Buchwald, Stephen L. Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination. Journal of the American Chemical Society. Department of Chemistry. Massachusetts Institute of Technology. Cambridge, USA 02139. Volume 137. Issue 30. Pages 9716-9721. 2015

  • ROUTE 3

    • 202112074197292483.jpg

    Tewari, Neera; Maheshwari, Nitin; Medhane, Roshan; Nizar, Hashim; Prasad, Mohan. A Novel Method for the Large Scale Synthesis of Cinacalcet Hydrochloride Using Iron Catalyzed C-C Coupling. Organic Process Research & Development. Chemical Research Division. Ranbaxy Research Laboratories. Haryana, India 122001. Volume 16. Issue 9. Pages 1566-1568. 2012

  • ROUTE 4

    • 202112074290470716.jpg

    Prediger, Patricia; da Silva, Allan Ribeiro; Correia, Carlos Roque Duarte. Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine. Tetrahedron. Instituto de Quimica, UNICAMP. Universidade Estadual de Campinas. Campinas, Brazil 13084-971. Volume 70. Issue 20. Pages 3333-3341. 2014

  • ROUTE 5

    • 202112077799568402.jpg

    Thiel, Oliver R.; Bernard, Charles; Tormos, Wanda; Brewin, Alan; Hirotani, Shuji; Murakami, Kazuo; Saito, Kenji; Larsen, Robert D.; Martinelli, Michael J.; Reider, Paul J. Practical synthesis of the calcimimetic agent, cinacalcet. Tetrahedron Letters. Chemistry. Research and Discovery, Amgen Inc. Thousand Oaks, CA, USA 91320-1799.Volume 49. Issue 1. Pages 13-15. 2008

  • ROUTE 6

    • 202112074374448957.jpg

    Lv, Honggui; Xiao, Li-Jun; Zhao, Dongbing; Zhou, Qi-Lin. Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with arylboron acids. ChemRxiv. State Key Laboratory and Institute of Elemento-Organic Chemistry College of Chemistry. Nankai University. Tianjin, Peop. Rep. China 300071. Pages 1-5. 2018

  • ROUTE 7

    • 202112074356154910.jpg

    Catozzi, Nicola; Cotarca, Livius; Foletto, Johnny; Forcato, Massimiliano; Giovanetti, Roberto; Soriato, Giorgio; Verzini, Massimo. Process for the preparation of cinacalcet hydrochloride using reduction, sulfonation and elimination as key steps. Assignee Zach System S.p.A., Italy. WO 2010094674. 2010

  • ROUTE 8

    • 202112077754706044.jpg

    Srinivasan, Chidambaram Venkateswaran; Johar, Perminder Singh; Wadhwa, Lalit. Process for preparation of cinacalcet hydrochloride. Assignee Ind-Swift Laboratories Limited, India. WO 2008035381. 2008

  • ROUTE 9

    • 202112074766461909.jpg

    Padi, Pratap Reddy; Akundi, Surya Prabhakar; Suthrapu, Sashi Kanth; Kolla, Naveen Kumar; Kotagiri, Vijaya Kumar; Neelam, Uday Kumar; Baddam, Sudhakar Reddy; Manne, Nagaraju; Devarakonda, Surya Narayana; Thaimattam, Ram; Raghupati, Balaji; Vasamsetti, Satish Kumar. Process for preparation of Cinacalcet hydrochloride. Assignee Dr. Reddy's Laboratories, Ltd., India; Dr. Reddy's Laboratories, Inc. WO 2008058236. 2008

  • ROUTE 10

    • 202112076644997763.jpg

    Hu, Changchun; Chen, Yanhui. A process for preparing cinacalcet hydrochloride. Assignee Shanghai Yong Yi Biotechnology Co., Ltd., Peop. Rep. China. WO 2012051737. 2012

202112077769066218.jpg

Arava, Veera R.; Gorentla, Laxminarasimhulu; Dubey, Pramod K. A novel asymmetric synthesis of cinacalcet hydrochloride. Beilstein Journal of Organic Chemistry. R&D Laboratory. Suven Life Sciences Ltd. Hyderabad, India. Volume 8. Pages 1366-1373, No. 158. 2012

226256-56-0 Synthesis
CINACALCET

226256-56-0
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Yield:364782-34-3 95%

Reaction Conditions:

with hydrogenchloride in n-heptane;ethyl acetate at 20;

Steps:

1.2 (2) Preparation of N-((1R)-1-(1-naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride (I)

It was dissolved in n-heptane solution (150mL),A 15% hydrochloric acid ethyl acetate solution was added dropwise at room temperature until no solid precipitated.Stir overnight at room temperature, filter, and filter cake washed with n-heptane.The filter cake was recrystallized from ethyl acetate, suction filtered and dried.Obtained white solid 10.47g,Is N-((1R)-1-(1-naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride (I),The yield was 95% and the HPLC detection was 99.98%.

References:

CN107879939,2018,A Location in patent:Paragraph 0075; 0078; 0079; 0083; 0084; 0088; 0089

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