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| | 4-chloro-7-Methoxyquinoline-6-carboxaMide Basic information |
| Product Name: | 4-chloro-7-Methoxyquinoline-6-carboxaMide | | Synonyms: | 6-QuinolinecarboxaMide, 4-chloro-7-Methoxy-;4-chloro-7-Methoxyquinoline-6-carboxaMide;4-chloro-7-Methoxy-6-QuinolinecarboxaMide;Lenvatinib Impurity b;Lenvatinib Impurity LFS-B;synthesis-024;4-Chloro-7-methoxy-quinoline-6-carboxylic acid amide;4-Chloro-7-methoxyquinazoline-6-carboxamide | | CAS: | 417721-36-9 | | MF: | C11H9ClN2O2 | | MW: | 236.65 | | EINECS: | 000-000-0 | | Product Categories: | Intermediate;417721-36-9 | | Mol File: | 417721-36-9.mol |  |
| | 4-chloro-7-Methoxyquinoline-6-carboxaMide Chemical Properties |
| Melting point | >205°C (dec.) | | Boiling point | 426.7±45.0 °C(Predicted) | | density | 1.380±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 15.28±0.30(Predicted) | | form | Solid | | color | Off-White to Light Beige | | InChI | InChI=1S/C11H9ClN2O2/c1-16-10-5-9-6(4-7(10)11(13)15)8(12)2-3-14-9/h2-5H,1H3,(H2,13,15) | | InChIKey | ZBTVNIDMGKZSGC-UHFFFAOYSA-N | | SMILES | N1C2C(=CC(C(N)=O)=C(OC)C=2)C(Cl)=CC=1 | | CAS DataBase Reference | 417721-36-9 |
| | 4-chloro-7-Methoxyquinoline-6-carboxaMide Usage And Synthesis |
| Description | 4-chloro-7-Methoxyquinoline-6-carboxaMide is a pharmaceutical intermediate compound used in the preparation of Lenvatinib, an oral multi-receptor tyrosine kinase inhibitor approved by the FDA for the treatment of radioiodine-refractory differentiated thyroid cancer (DTC), unresectable (DTC), unresectable hepatocellular carcinoma (HCC), and advanced renal cell carcinoma (RCC). | | Chemical Properties | light yellow powder | | Uses | Pharmaceutical Intermediates. 4-chloro-7-Methoxyquinoline-6-carboxaMide is used as an intermediate for synthesizing Lenvatinibis. | | Synthesis | General procedure for the synthesis of 4-chloro-7-methoxyquinoline-6-amide from methyl 4-chloro-7-methoxyquinoline-6-carboxylate: 4.1) Ammonia (200 mL, 5.2 mol) was added to a 500 mL three-necked flask, followed by the addition of Compound IV (10 g, 39.8 mmol) obtained from Step 3.3) to obtain Mixture H; 4.2) Mixture H was was reacted at 60 °C for 4 h. After completion of the reaction, the mixture was cooled to room temperature to obtain mixture I. 4.3) Three extractions were performed by adding dichloromethane to mixture I, resulting in a light yellow solid compound V in 85.17% yield. | | References | [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1668 - 1680
[2] Patent: CN107629001, 2018, A. Location in patent: Paragraph 0112; 0128-0131; 0164-0167; 0199-0202; 0235-0238
[3] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 48
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1649 - 1667 |
| | 4-chloro-7-Methoxyquinoline-6-carboxaMide Preparation Products And Raw materials |
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