Neratinib CAS#: 698387-09-6; ChemWhat Code: 100406
Identification
| Product Name | Neratinib |
| IUPAC Name | (E)-N-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide |
| Molecular Structure |  |
| CAS Registry Number | 698387-09-6 |
| EINECS Number | No data available |
| MDL Number | MFCD09752958 |
| Beilstein Registry Number | No data available |
| Synonyms | neratinibNeratinib(2E)-N-[4-({3-chloro-4-[(pyridin-2-yl)methoxy]phenyl}amino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)-2-butenamide(2E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide(E)-N-[4-((3-chloro-4-((pyridine-2-yl)methoxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide(E)-N-(4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-3-cyano-7-ethyloxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide(E)-N-[4-[[3-chloro-4-[(pyridin-2-yl)methoxy]phenyl]amino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide |
| Molecular Formula | C30H29ClN6O3 |
| Molecular Weight | 557.043 |
| InChI | InChI=1S/C30H29ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-12,14-16,18H,4,13,19H2,1-3H3,(H,34,35)(H,36,38)/b9-7+ |
| InChI Key | JWNPDZNEKVCWMY-VQHVLOKHSA-N |
| Canonical SMILES | CCOc1cc2c(cc1NC(=O)/C=C/CN(C)C)c(c(cn2)C#N)Nc3ccc(c(c3)Cl)OCc4ccccn4 |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| US2006/79515 | Method for the treatment of polycystic kidney disease | 2006 |
| US2006/270669 | Method of preparing 3-cyano-quinolines and intermediates made thereby | 2006 |
Physical Data
| Appearance | White to yellow powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 182 – 184 | acetonitrile, tetrahydrofuran |
| 178 – 183 |
| Density, g·cm-3 | Comment (Density) |
| 5.577E-08 | Press = 0.2 MPa |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 500 |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | |
| Chemical shifts | dimethylsulfoxide-d6 | 300 |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Temperature (IR Spectroscopy), °C |
| Bands | potassium bromide |
| Description (Mass Spectrometry) |
| electrospray ionisation (ESI), spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: (E)-4-(dimethylamino)-2-butenoic acid hydrochloride With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0 – 30℃; for 2h; Stage #2: 6-amino-4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-7-ethoxyquinoline-3-carbonitrile In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 – 5℃; for 3 – 16h; | 80% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Danger |
| GHS Hazard Statements | H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P201, P202, P281, P308+P313, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
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 49/g |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 557.052 |
| logP | 3.866 |
| HBA | 7 |
| HBD | 2 |
| Matching Lipinski Rules | 3 |
| Veber rules component | |
| Polar Surface Area (PSA) | 112.4 |
| Rotatable Bond (RotB) | 12 |
| Matching Veber Rules | 1 |
| Use Pattern |
| Neratinib CAS#: 698387-09-6 a tyrosine kinase inhibitor for prolonged adjuvant treatment of early-stage HER2-positive breast cancer. |
| Neratinib CAS#: 698387-09-6 |
| Neratinib CAS#: 698387-09-6 |
| Neratinib CAS#: 698387-09-6 |
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Approved Manufacturers | |
| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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