848133-87-9

Basic information

• Product Name: 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE
• Synonyms: 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE;3-Quinolinecarbonitrile, 6-aMino-4-chloro-7-ethoxy-;6-Amino-4-chloro-7-ethoxy-3-quinolinecarbonitrile
• CAS NO: 848133-87-9
• Molecular Formula: C₁₂H₁₀ClN₃O
• Molecular Weight: 247.6803
• Product Categories: Intermediates
• Mol File: 848133-87-9.mol

Chemical Properties

• Boiling Point: 453.7°C at 760 mmHg
• Flash Point: 228.2°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 2.02E-08mmHg at 25°C
• Refractive Index: 1.654
• PKA: 1.35±0.41(Predicted)
• CAS DataBase Reference: 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE(848133-87-9)
• EPA Substance Registry System: 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE(848133-87-9)

Safety Data

• Hazardous Substances Data: 848133-87-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE is used as a chemical intermediate for the synthesis of quinoline and naphthyridine derivatives with potent antitumor properties. Its role in the development of new anticancer agents is crucial, as these derivatives have demonstrated significant activity against various types of cancer.
In the study for synthesis and structure-activity relationships, 6-AMINO-4-CHLORO-7-ETHOXYQUINOLINE-3-CARBONITRILE has been instrumental in understanding the relationship between the molecular structure of quinoline and naphthyridine derivatives and their antitumor activity. This knowledge is essential for the design and development of more effective and targeted cancer therapies.

InChI:InChI=1/C12H10ClN3O/c1-2-17-11-4-10-8(3-9(11)15)12(13)7(5-14)6-16-10/h3-4,6H,2,15H2,1H3

Upstream product

• 214476-08-1 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile 
• 116435-75-7 3-(ethyloxy)-4-nitroaniline 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 214476-09-2 4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile 

Downstream Products

• 848133-88-0 4-chloro-6-(5-(dimethylamino)-2-oxopent-3-enyl)-7-ethoxyquinoline-3-carbonitrile 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 848133-14-2 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile 

Relevant articles and documents

1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS

Compositions of the invention comprise 1,2-dithiolane, dithiol and related compounds useful as therapeutic agents for the treatment and prevention of diseases and conditions associated with aberrant EGFR activity.

A method of synthesizing a neratinib intermediate, 3-cyano-4-chloro-6-amino-7-ethoxyquinoline

A method of synthesizing a neratinib intermediate that is 3-cyano-4-chloro-6-amino-7-ethoxyquinoline is disclosed. The method includes (1) subjecting methyl 4-ethoxy-2-chloro-5-nitrobenzoate and 3-amino acrylonitrile to a condensation reaction under the action of a catalyst 1 to obtain 2-(4-ethoxy-2-chloro-5-nitrobenzoyl)-3-amino acrylonitrile; (2) subjecting the 2-(4-ethoxy-2-chloro-5-nitrobenzoyl)-3-amino acrylonitrile to a cyclization reaction to obtain 3-cyano-4-oxo-6-nitro-7-ethoxy-1,4-dihydroquinoline; (3) subjecting the 3-cyano-4-oxo-6-nitro-7-ethoxy-1,4-dihydroquinoline and phosphorus oxychloride to a chlorination reaction to obtain 3-cyano-4-chloro-6-nitro-7-ethoxyquinoline; and (4) subjecting the 3-cyano-4-chloro-6-nitro-7-ethoxyquinoline and hydrazine hydrate to a reduction reaction under the action of a catalyst 2 to obtain a target product. According to the method, synthetic steps are few, reaction conditions are mild, agents are cheap and easily available, operation is simple and the total yield is high. The method provides a novel route for preparation of neratinib and the intermediate.

COMPOSITION AND METHODS FOR INHIBITING MAMMALIAN STERILE 20-LIKE KINASE 1

Disclosed herein are compounds, compositions, and methods of their use for the treatment of diabetes.

Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity

A series of new 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitrile derivatives that function as irreversible inhibitors of human epidermal growth factor receptor-2 (HER-2) and epidermal growth factor receptor (EGFR) kinases have been prepared. These compounds demonstrated enhanced activities for inhibiting HER-2 kinase and the growth of HER-2 positive cells compared to our EGFR kinase inhibitor 86 (EKB-569). Three synthetic routes were used to prepare these compounds. They were prepared mostly by acylation of 6-amino-4-(arylamino) quinoline-3-carbonitriles with unsaturated acid chlorides or by amination of 4-chloro-6-(crotonamido)-quinoline-3-carbonitriles with monocyclic or bicyclic anilines. The third route was developed to prepare a key intermediate, 6-acetamido-4-chloroquinoline-3-carbonitrile, that involved a safer cyclization step. We show that attaching a large lipophilic group at the para position of the 4-(arylamino) ring results in improved potency for inhibiting HER-2 kinase. We also show the importance of a basic dialkylamino group at the end of the Michael acceptor for activity, due to intramolecular catalysis of the Michael addition. This, along with improved water solubility, resulted in compounds with enhanced biological properties. We present molecular modeling results consistent with the proposed mechanism of inhibition. Binding studies of one compound, 25o (C-14 radiolabeled), showed that it binds irreversibly to HER-2 protein in BT474 cells. Furthermore, it demonstrated excellent oral activity, especially in HER-2 overexpressing xenografts. Compound 25o (HKI-272) was selected for further studies and is currently in phase I clinical trials for the treatment of cancer.