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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List Binimetinib

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).

4-Bromo-2-fluoro-1-iodobenzene

105931-73-5
349 suppliers
$5.00/5g

Binimetinib

606143-89-9
177 suppliers
$45.00/5mg

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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

5-((4-bromo-2-fluorophenyl)amino)-N-(2-(tert-butoxy)ethoxy)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxamide

1604812-70-5
10 suppliers
inquiry

Binimetinib

606143-89-9
177 suppliers
$45.00/5mg

References
5-((4-broMo-2-fluorophenyl)aMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylic acid

1415564-99-6
21 suppliers
inquiry

Binimetinib

606143-89-9
177 suppliers
$45.00/5mg

References
Methyl 5-aMino-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate

918321-20-7
85 suppliers
$13.00/100mg

Binimetinib

606143-89-9
177 suppliers
$45.00/5mg

References
methyl 5-((4-bromo-2-fluorophenyl)amino)-4-fluoro-1H-benzo[d]imidazole-6-carboxylate

606143-48-0
26 suppliers
inquiry

Binimetinib

606143-89-9
177 suppliers
$45.00/5mg

References

Binimetinib Related Search:

PD 0325901 Selumetinib Anacetrapib LasMiditan BMS-794833 R428 Tozasertib