361162-95-0

Basic information

• Product Name: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile
• Synonyms: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile;6-AMino-4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethyloxyquinoline;6-AMino-4-[(3-chloro-4-fluorophenyl)aMino]-7-ethoxy-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 6-aMino-4-[(3-chloro-4-fluorophenyl)aMino]-7-ethoxy-
• CAS NO: 361162-95-0
• Molecular Formula: C₁₈H₁₄ClFN₄O
• Molecular Weight: 357
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 361162-95-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 533.385°C at 760 mmHg
• Flash Point: 276.382°C
• Appearance: /
• Density: 1.421g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(361162-95-0)
• EPA Substance Registry System: 6-amino-4-(3-chloro-4-fluorophenylamino)-7-ethoxyquinoline-3-carbonitrile(361162-95-0)

Safety Data

• Hazardous Substances Data: 361162-95-0(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of Tyrosine Kinase Inhibitors.

InChI:InChI=1/C18H14ClFN4O/c1-2-25-17-7-16-12(6-15(17)22)18(10(8-21)9-23-16)24-11-3-4-14(20)13(19)5-11/h3-7,9H,2,22H2,1H3,(H,23,24)

Upstream product

• 1313378-64-1 N-[4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]acetamide hydrochloride 
• 915945-40-3 3-cyano-4-(3-chloro-4-fluoroanilino)-7-ethoxy-N-phthalimidyl-quinoline 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 848133-87-9 6-amino-4-chloro-7-ethoxyquinoline-3-carbonitrile 
• 848133-74-4 3-(4-acetamido-3-ethoxyaniline)-2-cyanopropenoic acid ethyl ester 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 848655-78-7 4-acetamido-3-ethoxyaniline 
• 116496-76-5 4-acetamido-3-ethoxynitrobenzene 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 1201080-09-2 N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide 
• 848655-77-6 N-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl)acetamide 
• 7439-89-6 iron 
• 492456-51-6 (E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester 
• 214476-08-1 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile 

Downstream Products

• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1245710-93-3 (E)-4-[(4-fluorobenzyl)methylamino]-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl] amide 
• 1245710-91-1 (E)-4-[(2-fluoroethyl)methylamino]-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]amide 
• 1245711-05-0 (E)-4-(methylamino)-but-2-enoic acid [4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl]amide hydrochloride 

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.

Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides

Irreversible epidermal growth factor receptor (EGFR) inhibitors contain a reactive warhead which covalently interacts with a conserved cysteine residue in the kinase domain. The acrylamide fragment, a commonly employed warhead, effectively alkylates Cys797 of EGFR, but its reactivity can cause rapid metabolic deactivation or nonspecific reactions with off-targets. We describe here a new series of irreversible inhibitors containing a 3-aminopropanamide linked in position 6 to 4-anilinoquinazoline or 4-anilinoquinoline-3- carbonitrile driving portions. Some of these compounds proved to be as efficient as their acrylamide analogues in inhibiting EGFR-TK (TK = tyrosine kinase) autophosphorylation in A549 lung cancer cells. Moreover, several 3-aminopropanamides suppressed proliferation of gefitinib-resistant H1975 cells, harboring the T790M mutation in EGFR, at significantly lower concentrations than did gefitinib. A prototypical compound, N-(4-(3-bromoanilino)quinazolin-6- yl)-3-(dimethylamino)propanamide (5), did not show covalent binding to cell-free EGFR-TK in a fluorescence assay, while it underwent selective activation in the intracellular environment, releasing an acrylamide derivative which can react with thiol groups.

Process for the synthesis of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile

The present invention provides a process for the preparation of 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile comprising the steps and products disclosed within this application.