| Identification | Back Directory | [Name]
4-chloro-7-Methoxyquinoline-6-carboxaMide | [CAS]
417721-36-9 | [Synonyms]
lenvaint-E
Lenvatinib Impurity b
4-chloro-7-Methoxyquinoline-6-carboxaMide
4-chloro-7-Methoxy-6-QuinolinecarboxaMide
6-QuinolinecarboxaMide, 4-chloro-7-Methoxy-
4-Chloro-7-methoxyquinazoline-6-carboxamide
4-Chloro-7-methoxy-quinoline-6-carboxylic acid amide | [EINECS(EC#)]
-0 | [Molecular Formula]
C11H9ClN2O2 | [MDL Number]
MFCD13192256 | [MOL File]
417721-36-9.mol | [Molecular Weight]
236.654 |
| Chemical Properties | Back Directory | [Melting point ]
>205°C (dec.) | [Boiling point ]
426.7±45.0 °C(Predicted) | [density ]
1.380±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
15.28±0.30(Predicted) | [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 |
| Hazard Information | Back Directory | [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]
4-chloro-7-methoxyquinoline-6-amide is a light yellow solid substance, mainly used as an intermediate for lenvatinib. | [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 |
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