Binimetinib CAS#: 606143-89-9; 凯望编码 (ChemWhat Code): 1370890
Identification
| 英文名 | Binimetinib |
| IUPAC Name | 6-(4-bromo-2-fluoroanilino)-7-fluoro-N-(2-hydroxyethoxy)-3-methylbenzimidazole-5-carboxamide |
| 分子结构 |  |
| CAS编号 | 606143-89-9 |
| 别名 | 6-(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 |
| 分子式 | C17H15BrF2N4O3 |
| 分子量 | 441.2268064 |
| InChI | InChI=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 SMILES | CN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)F)C(=O)NOCCO |
| Patent Information | ||
| Patent ID | Title | Publication 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
| Appearance | White or off-white crystalline powder |
| Acidity coefficient (pKa) | 14.20±0.10(Predicted) |
| Density | 1.67 |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 400 |
| Binimetinib CAS 606143-89-9 HNMR |  |
Route of Synthesis (ROS)
| Conditions | Yield |
| 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 Statements | Not Classified |
Other Data
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 years |
| Market Price | USD 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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认证生产商 | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
| Array BioPharma | https://www.arraybiopharma.com/ |
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| Watson International Limited | 访问Watson官网 |
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