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ChemicalBook CAS DataBase List Binimetinib
606143-89-9

Binimetinib synthesis

10synthesis methods
Binimetinib, also known as MEK162 (ARRY-162), is an oral, highly selective MEK inhibitor. In preclinical studies, MEK162 showed significant antitumor activities in cell lines and animal models. MEK162 is the first targeted therapy to show activity in patients with NRAS -mutated melanoma and might offer a new option for a cancer with few effective treatments.
Synthetic Routes
  • ROUTE 1

    • 202112073319677728.jpg

    Anon. Process for the preparation of 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1-methyl-1H-benz[d]imidazole-6-carboxylic acid. IP.com Journal. Volume 15. Issue 12B. Pages 1pp.Journal; Patent. (2015).

  • ROUTE 2

    • 202112070472855917.jpg

    Chen, Jian. Synthetic method of Binimetinib. Assignee Hunan Ouya Biological Co., Ltd., Peop. Rep. China. CN 105820124. (2016).

  • ROUTE 3

    • 202112079866324962.jpg

    Huang, Xizhong; Peters, Malte; Schumacher, Karl Maria; Cao, Zhu Alexander; Gansert, Jennifer Lorraine; Chang, David Dong Eun; Beltran, Pedro. Combination therapy. Assignee Novartis Pharma AG, Switz.; Amgen Inc. WO 2013142182. (2013).

  • ROUTE 4

    • 202112077723318339.jpg

    Wallace, Eli M.; Lyssikatos, Joseph P.; Marlow, Allison L.; Hurley, T. Brian; Koch, Kevin. Preparation of phenylaminobenzimidazolecarboxylates as mitogen activated protein kinase kinase (MEK) inhibitors. Assignee Array BioPharma, Inc., USA. US 20040116710. (2004).

202112073319677728.jpg

Anon. Process for the preparation of 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1-methyl-1H-benz[d]imidazole-6-carboxylic acid. IP.com Journal. Volume 15. Issue 12B. Pages 1pp.Journal; Patent. (2015).

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Yield:-

Steps:

Multi-step reaction with 5 steps
1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene; 1,4-dioxane / 8 h / 99 °C / Inert atmosphere
2: potassium trimethylsilonate / N,N-dimethyl-formamide; tetrahydrofuran / 1.67 h / 20 - 25 °C / Inert atmosphere
3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 - 50 °C
4: N,N-dimethyl-formamide; tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
5: phosphoric acid; water / acetonitrile / 6.25 h / 20 - 53 °C

References:

NOVARTIS AG;ARRAY BIOPHARMA INC.;KRELL, Christoph, Max;MISUN, Marian;NIEDERER, Daniel, Andreas;PACHINGER, Werner, Heinz;WOLF, Marie-christine;ZIMMERMANN, Daniel;LIU, Weidong;STENGEL, Peter, J.;NICHOLS, Paul WO2014/63024, 2014, A1

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