ChemicalBook CAS DataBase List Binimetinib

Binimetinib synthesis

10synthesis methods

Product Name:Binimetinib
CAS Number:606143-89-9
Molecular formula:C17H15BrF2N4O3
Molecular Weight:441.23

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

ROUTE 2

ROUTE 3

ROUTE 4

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