214476-09-2

Basic information

• Product Name: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline
• Synonyms: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline;4-Chloro-7-ethoxy-6-nitro-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 4-chloro-7-ethoxy-6-nitro-;4-chloro-7-ethoxy-6-nitroquinoline-3-carbonitrile
• CAS NO: 214476-09-2
• Molecular Formula: C₁₂H₈ClN₃O₃
• Molecular Weight: 277.66322
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Tyrosine Kinase Inhibitors
• Mol File: 214476-09-2.mol

Chemical Properties

• Boiling Point: 485.3°C at 760 mmHg
• Flash Point: 247.3°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 1.43E-09mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO
• PKA: -1.04±0.41(Predicted)
• CAS DataBase Reference: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(214476-09-2)
• EPA Substance Registry System: 4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline(214476-09-2)

Safety Data

• Hazardous Substances Data: 214476-09-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-3-cyano-7-ethoxy-6-nitroquinoline is used as a key intermediate in the synthesis of tyrosine kinase inhibiting antitumor agents. Its chemical structure allows it to interact with specific protein targets, such as tyrosine kinases, which play a crucial role in cell signaling and are often dysregulated in cancer cells. By inhibiting these enzymes, the compound can help in the development of targeted therapies for various types of cancer.
The compound's unique structure and functional groups also make it a promising candidate for further research and development in the pharmaceutical industry, potentially leading to the discovery of new drugs with improved efficacy and selectivity.

InChI:InChI=1/C12H8ClN3O3/c1-2-19-11-4-9-8(3-10(11)16(17)18)12(13)7(5-14)6-15-9/h3-4,6H,2H2,1H3

Upstream product

• 214476-07-0 7-ethoxy-4-hydroxyquinoline-3-carbonitrile 
• 361162-91-6 5-ethoxy-2-methyl-4-nitroacetanilide 
• 909513-02-6 (E)-2-Cyano-3-(3-ethoxy-phenylamino)-acrylic acid ethyl ester 
• 361162-92-7 2-acetylamino-4-ethoxy-5-nitrobenzoic acid 
• 492456-51-6 (E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester 
• 621-33-0 m-phenetidine 
• 848133-75-5 3-cyano-4-hydroxyl-6-acetamido-7-ethoxyquinoline 
• 10026-13-8 phosphorus pentachloride 
• 214476-08-1 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile 
• 2369-13-3 3-fluoro-4-nitroaniline 
• 361162-90-5 5-methoxy-2-methyl-4-nitroacetanilide 
• 116435-75-7 3-(ethyloxy)-4-nitroaniline 
• 106579-00-4 5-methoxy-2-methyl-4-nitroaniline 

Downstream Products

• 263171-30-8 4-[3-chloro-4-(1H-imidazol-1-ylmethyl) anilino]-7-ethoxy-6-nitro-3-quinolinecarbonitrile 
• 263171-08-0 4-[3-chloro-4-(4-pyridinyloxy)anilino]-7-ethoxy-6-nitro-3-quinolinecarbonitrile 
• 848133-87-9 6-amino-4-chloro-7-ethoxyquinoline-3-carbonitrile 
• 848133-88-0 4-chloro-6-(5-(dimethylamino)-2-oxopent-3-enyl)-7-ethoxyquinoline-3-carbonitrile 
• 848133-69-7 6-amino-4-(3-benzyloxy-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 263171-09-1 6-amino-4-[3-chloro-4-(4-pyridinyloxy)anilino]-7-ethoxy-3-quinolinocarbonitrile 
• 848133-66-4 6-amino-4-[3-chloro-4-(thiophen-2-ylmethoxy)-phenylamino]-7-ethoxy-quinoline-3-carbonitrile 
• 544417-29-0 6-amino-4-(4-benzyloxy-3-chlorophenylamino)-7-ethoxyquinoline-3-carbonitrile 
• 848133-15-3 6-amino-4-(3-chloro-4-morpholin-4-yl-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 848133-70-0 6-amino-4-[4-(benzyl-methyl-amino)-3-chloro-phenylamino]-7-ethoxy-quinoline-3-carbonitrile 

Relevant articles and documents

NITROGENOUS HETEROCYCLIC COMPOUND, PREPARATION METHOD, INTERMEDIATE, COMPOSITION, AND APPLICATION

A nitrogenous heterocyclic compound, a preparation method, an intermediate, a composition, and an application. The present invention provides a nitrogenous heterocyclic compound as represented by formula I, pharmaceutically acceptable salts thereof, enantiomers thereof, diastereoisomers thereof, tautomers thereof, solvates thereof, metabolites thereof, or prodrugs thereof. The compound has high inhibitory activity against ErbB2 tyrosine kinase, has good inhibitory activity against human breast cancer cells BT-474, human gastric cancer cells NCI-N87 and the like with high expression of ErbB2, and in addition has relatively weak inhibitory activity against EGFR kinase, that is, the compound is an EGFR/ErbB2 double target inhibitor that attenuates EGFR kinase inhibitory activity or a small-molecule inhibitor having selectivity for an ErbB2 target. (I)

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.

Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors

This invention provides compounds of formula 1 wherein R1, G1, G2, R4, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof, which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

USE OF CYANOQUINOLINES FOR TREATING OR INHIBITING COLONIC POLYPS

This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula (1); wherein R1, R2, R3, R4, X, Y, and n are defined hereinbefore, or a pharmaceutically acceptable salt thereof.

SUBSTITUTED QUINOLINES AS PROTEIN TYROSINE KINASE ENZYME INHIBITORS

This invention provides compounds of formula (I), having the structure wherein R1, R2, R3 are described within the specification. The compounds act as anti-cancer agents by inhibition of HER-2 and EGFR.

Synthesis and structure-activity relationships of 6,7-disubstituted 4-anilinoquinoline-3-carbonitriles. The design of an orally active, irreversible inhibitor of the tyrosine kinase activity of the epidermal growth factor receptor (EGFR) and the human epi

A series of of 6,7-disubstituted-4-anilinoquinoline-3-carbonitrile derivatives that function as irreversible inhibitors of EGFR and HER-2 kinases have been prepared. These inhibitors have, at the 6-position, butynamide, crotonamide, and methacrylamide Mic

SUBSTITUTED 3-CYANOQUINOLINES AS PROTEIN TYROSINE KINASES INHIBITORS

This invention provides compounds of formula (1) wherein R1, G1, G2, R4, Z, X and n are defined herein, or a pharmaceutically acceptable salt thereof, which are useful as antineoplastic agents and in the treatment of polycystic kidney disease.

SUBSTITUTED 3-CYANO QUINOLINES

This invention provides compounds having formula (1), wherein: X is cycloalkyl which may be optionally substituted; or is a pyridinyl, pyrimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally substituted; n is 0-1; Y is -NH-, -O-, -S-, or -NR-; R is alkyl of 1-6 carbon atoms; R1, R2, R3 and R4 are each, independently, hydrogen, halogen, alkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, hydroxymethyl, halomethyl, alkanoyloxy, alkenoyloxy, alkynoyloxy, alkanoyloxymethyl, alkenoyloxymethyl, alkynoyloxymethyl, alkoxymethyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylsulfonamido, alkenylsulfonamido, alkynylsulfonamido, hydroxy, trifluoromethyl, cyano, nitro, carboxy, carboalkoxy, carboalkyl, phenoxy, phenyl, thiophenoxy, benzyl, amino, hydroxyamino, alkoxyamino, alkylamino, dialkylamino, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, phenylamino, benzylamino, formulae (a, b, c, d, e, f, g, h, i, j, k, l, m, n, o, p, q or r); R5 is alkyl which may be optionally substituted, or phenyl which may be optionally substituted; R6 is hydrogen, alkyl, or alkenyl; R7 is chloro or bromo; R8 is hydrogen, alkyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, N-cycloalkylaminoalkyl, N-cycloalkyl-N-alkylaminoalkyl, N,N-dicycloalkylaminoalkyl, morpholino-N-alkyl, piperidino-N-alkyl, N-alkyl-piperidino-N-alkyl, azacycloalkyl-N-alkyl, hydroxyalkyl, alkoxyalkyl, carboxy, carboalkoxy, phenyl, carboalkyl +, chloro, fluoro, or bromo; Z is amino, hydroxy, alkoxy, alkylamino, dialkylamino, morpholino, piperazino, N-alkylpiperazino, or pyrrolidino; m = 1-4, q = 1-3, and p = 0-3; any of the substituents R1, R2, R3 or R4 that are located on contiguous carbon atoms can together be the divalent radical -O-C(R8)2-O-; or a pharmaceutically acceptable salt thereof with the proviso that when Y is -NH-, R1, R2, R3 and R4 are hydrogen, and n is O, X is not 2-methylphenyl, which are inhibitors of protein tyrosine kinase.

Method of treating or inhibiting colonic polyps

This invention provides a method of treating or inhibiting colonic polyps which comprises providing a compound of formula 1 wherein:R1, R2, R3, R4, X, Y, and n are as defined hereinbefore, or a pharmaceutically acceptable salt thereof.