Methyl 5-(4-broMo-2-chlorophenylaMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate CAS#: 606144-02-9; ChemWhat Code: 979389
Identification
| Product Name | Methyl 5-(4-broMo-2-chlorophenylaMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate |
| IUPAC Name | methyl 6-(4-bromo-2-chloroanilino)-7-fluoro-3-methylbenzimidazole-5-carboxylate |
| Molecular Structure | ![Structure of Methyl 5-((4-bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate CAS 606144-02-9](https://www.chemwhat.com/wp-content/uploads/2018/04/Structure-of-Methyl-5-4-bromo-2-chlorophenylamino-4-fluoro-1-methyl-1H-benzodimidazole-6-carboxylate-CAS-606144-02-9.png) |
| CAS Registry Number | 606144-02-9 |
| EINECS Number | No data available |
| MDL Number | MFCD09910413 |
| Beilstein Registry Number | No data available |
| Synonyms | 1H-Benzimidazole-6-carboxylic acid, 5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-1-methyl-, methyl ester 5-[(4-Bromo-2-chlorophényl)amino]-4-fluoro-1-méthyl-1H-benzimidazole-6-carboxylate de méthyle Methyl 5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylate Methyl-5-[(4-brom-2-chlorphenyl)amino]-4-fluor-1-methyl-1H-benzimidazol-6-carboxylat |
| Molecular Formula | C16H12BrClFN3O2 |
| Molecular Weight | 412.64 |
| InChI | InChI=1S/C16H12BrClFN3O2/c1-22-7-20-15-12(22)6-9(16(23)24-2)14(13(15)19)21-11-4-3-8(17)5-10(11)18/h3-7,21H,1-2H3 |
| InChI Key | WXGUDZJZWDZKBV-UHFFFAOYSA-N |
| Canonical SMILES | Cn1cnc2c1cc(c(c2F)Nc3ccc(cc3Cl)Br)C(=O)OC |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| WO2018/65924 | INTERMEDIATES OF MITOGEN-ACTIVATED PROTEIN KINASE KINASE (MAP2K OR MEK) INHIBITORS AND PROCESS FOR THEIR PREPARATION | 2018 |
| WO2007/2157 | PROCESS FOR PREPARING BENZIMIDAZOLE COMPOUNDS | 2007 |
| US2004/116710 | N3 ALKYLATED BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS | 2004 |
| US2003/232869 | N3 ALKYLATED BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS | 2003 |
Physical Data
| Appearance | White powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz | Original Text (NMR Spectroscopy) |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 400 | 1HNMR(d6-DMSO, 400 MHz): 3.83 (s, 3H), 3.93 (s, 3H), 6.42-6.45 (m, 1H), 7.27-7.30 (m, 1H), 7.63-7.64 (d, 1H), 8.10 (s, 1H), 8.14 (s, 1H), 8.46 (s, 1H). |
| 19F | d(4)-methanol | 376 | 19F NMR (376 MHz, CD3OD) – 133.5(s). | |
| 19F | d(4)-methanol | 19F NMR (376 MHz, CD3OD) – 133.5(s). | ||
| 19F | d(4)-methanol | 19F NMR (376 MHz, CD3OD) – 133.5(s). |
| Original Text (IR Spectroscopy) |
| v^/cm“1 3401, 1700, 1506, 1274; |
| Description (Mass Spectrometry) | Comment (Mass Spectrometry) |
| spectrum | |
| CI (Chemical ionization) | Molecular peak |
| Appearance potentials, CI (Chemical ionization) | Molecular peak |
Route of Synthesis (ROS)
![Route of Synthesis (ROS) of Methyl 5-(4-broMo-2-chlorophenylaMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate CAS 606144-02-9](https://www.chemwhat.com/wp-content/uploads/2018/04/Route-of-Synthesis-ROS-of-Methyl-5-4-broMo-2-chlorophenylaMino-4-fluoro-1-Methyl-1H-benzodiMidazole-6-carboxylate-CAS-606144-02-9.png)
| Conditions | Yield |
| With hydrogen In ethyl acetate at 20℃; under 7600.51 Torr; for 6h; Autoclave; | 99% |
| With 0.2C27H36N2*Pt; hydrogen In tetrahydrofuran at 60℃; under 3000.3 Torr; for 5h; chemoselective reaction; | 99% |
| With hydrogen In ethyl acetate under 760.051 Torr; for 2h; Heating; Flow reactor; Green chemistry; | 99% |
| With hydrogen; triethylamine In ethanol; water at 110℃; under 30003 Torr; for 24h; Autoclave; | 98% |
| With hydrogen In 2-methyltetrahydrofuran; water at 40℃; under 15001.5 Torr; for 24h; chemoselective reaction; | 98% |
| With sodium tetrahydroborate In water at 20℃; for 1.5h; chemoselective reaction; Experimental Procedure General procedure: In a typical experiment, 0.5mmol of nitroarene and 0.002g(2mol%) NiNPs/DNA were added to 2mL water and thenstirred for 2-3min for thoroughly mixing. Subsequently,1mmol of NaBH4was added to the reaction mixture undermagnetic stirring at room temperature. The extent of thereaction was monitored by thin layer chromatography.Reproducibility of the results was checked by repeating theruns at least three times and was found to be within acceptablelimits (± 3%). When the reaction was completed, thereaction mixture was diluted with ethyl acetate and the catalystwas recovered by centrifugation. The combined organicfractions were dried over Na2SO4and evaporated underreduced pressure. The crude product was purified by columnchromatography on silica gel with a mixture of ethyl acetateand n-hexane as the eluent, and the ratio of ethyl acetate andn-hexane was depended on the structure of the products.The structure of isolated products was verified by 1H NMR. | 97% |
Safety and Hazards
| GHS Hazard Statements | Not Classified |
| For more detailed information, please visit ECHA C&L website |
| Source: European Chemicals Agency (ECHA) License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. License URL: https://echa.europa.eu/web/guest/legal-notice Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446 Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | No data available |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 412.646 |
| logP | 4.779 |
| HBA | 5 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 56.15 |
| Rotatable Bond (RotB) | 4 |
| Matching Veber Rules | 2 |
| Use Pattern |
| Methyl 5-(4-broMo-2-chlorophenylaMino)-4-fluoro-1-Methyl-1H-benzo[d]iMidazole-6-carboxylate CAS#: 606144-02-9 used as the Intermediate of Smetinib. |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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