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

Safety Information

HS Code 

2933499090

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(417721-36-9)Related Product Information

• 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxaMide
• 1-(2-chloro-4-hydroxyphenyl)-3-cyclopropylurea
• 7-methoxy-4-chloro-quinoline-6-carbonyl chloride
• Clioquinol
• Lansoprazole
• L-Glutamine, phenylmethyl ester
• 2-AMINOMETHYLPYRIMIDINE HYDROCHLORIDE
• λ-Cyhalothrin
• synthesis-020
• synthesis-022
• Lenvatinib Impurity d
• Lenvatinib Impurity 12
• Lenvatinib Impurity g
• 4-Amino-3-chlorophenol hydrochloride
• lenvatinib Mesylate
• Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate
• Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate
• 4-Amino-3-chlorophenol