Binimetinib CAS#: 606143-89-9

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameBinimetinib
IUPAC Name6-(4-bromo-2-fluoroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide
Molecular Structure
CAS Registry Number 606143-89-9
Synonyms6-(4-bromo-2-fluoro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide, 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxyethoxy)-amide, 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid-(2-hydroxyethyoxy)amide, 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxyethoxy)amide, 6-(4-bromo-2-fluoroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide, binimetinib, bnimetinib
Molecular FormulaC17H15BrF2N4O3
Molecular Weight441.2268064
InChIInChI=1S/C17H15BrF2N4O3/c1-24-8-21-16-13(24)7-10(17(26)23-27-5-4-25)15(14(16)20)22-12-3-2-9(18)6-11(12)19/h2-3,6-8,22,25H,4-5H2,1H3,(H,23,26)
InChIKey ACWZRVQXLIRSDF-UHFFFAOYSA-N
Canonical SMILESCN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)F)C(=O)NOCCO
Patent Information
Patent IDTitlePublication Date
US2014/341902 METHODS OF TREATING CANCER USING PD-1 AXIS BINDING ANTAGONISTS AND MEK INHIBITORS 2014
US2004/116710 N3 ALKYLATED BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS 2014
US2003/232869 N3 ALKYLATED BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS 2003

Physical Data

AppearanceWhite or off-white crystalline powder
Acidity coefficient (pKa)14.20±0.10(Predicted)
Density1.67

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum 1Hdimethylsulfoxide-d6 400
Binimetinib CAS 606143-89-9 HNMRBinimetinib CAS 606143-89-9 HNMR

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Binimetinib CAS 606143-89-9
Route of Synthesis (ROS) of Binimetinib CAS 606143-89-9
ConditionsYield
With phosphoric acid; water In acetonitrile at 20 – 53℃; for 6.25h;

Experimental Procedure
6-(4-Bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5- carboxylic acid-(2-tert-butoxyethoxy)-amide (Compound 5) monohydrate is added in 3 portions to a premixed solution of Acetonitrile and excess Phosphoric acid (85 percent aqueous solution) at internal temperature 20-25 °C. After stirring for about 15 minutes, the suspension is heated to internal temperature 50-53 °C. The suspension is maintained at this temperature for 6 hours, cooled to internal temperature 20-25 °C. The mixture is then heated to internal temperature 35-37°C and diluted with Ethanol- Water (3 :1 v/v). EKNS and CEFOK are added, the reaction mixture is stirred approximately 15 minutes and filtered over a funnel coated with CEFOK. The filtrate is cooled to approximately 30°C. 3 N aqueous potassium hydroxide (ΚΟΗ) is added to the cooled filtrate over a period of 90 minutes until a pH- value of about 8.1 is reached. The suspension is heated to internal temperature 60-63 °C, stirred at this temperature for a period of about 2 hours, cooled to 20-23 °C over a period of about 45 minutes, filtered over a funnel, and dried at 50°C pressure <100 mbar over a period of about 17 hours, providing 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H- benzoimidazole-5-carboxylic acid (2-hydroxyethyoxy)-amide (Compound A) as a white powder.

Safety and Hazards

GHS Hazard StatementsNot Classified

Other Data

TransportationNot dangerous goods
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life1 years
Market PriceUSD 180/g
Use Pattern
Acaricide
JMML tumor
Pharmaceuticals
Scwannoma
a myelodysplastic syndromes
adenoid and ovarian sereous cystadenocarcinoma
cancer of the upper aerodigestive tract
cancer of autonomic ganglia

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