214470-68-5

Basic information

• Product Name: 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE
• Synonyms: 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE;4-Chloro-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline;4-Chloro-7-(3-chloropropoxy)-3-cyano-6-methyloxyquinoline;4-Chloro-7-(3-chloropropoxy)-6-methoxy-3-quinolinecarbonitrile;7-(3-chloro-propoxy)-4-chloro-6-Methoxy-quinoline-3-carbonitrile;3-Quinolinecarbonitrile, 4-chloro-7-(3-chloropropoxy)-6-Methoxy-
• CAS NO: 214470-68-5
• Molecular Formula: C₁₄H₁₂Cl₂N₂O₂
• Molecular Weight: 311.16328
• EINECS: 1592732-453-0
• Product Categories: Intermediates
• Mol File: 214470-68-5.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 478.1°C at 760 mmHg
• Flash Point: 243°C
• Appearance: /
• Density: 1.37
• Vapor Pressure: 2.64E-09mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 0.57±0.41(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE(214470-68-5)
• EPA Substance Registry System: 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE(214470-68-5)

Safety Data

• Hazardous Substances Data: 214470-68-5(Hazardous Substances Data)

Usage

Description

4-Chloro-7-(3-chloropropoxy)-6-methoxy-quinoline-3-carbonitrile is an organic compound characterized by its quinoline structure with specific substitutions that contribute to its chemical properties and potential applications. It is a derivative of quinoline, a nitrogen-containing bicyclic compound, with a carbonitrile group, a methoxy group, and two chloro substituents on different positions of the molecule.

Uses

Used in Pharmaceutical Industry:
4-Chloro-7-(3-chloropropoxy)-6-methoxy-quinoline-3-carbonitrile is used as a chemical intermediate for the green preparation of the anti-tumor medication Bosutinib (B676095). 4-CHLORO-7-(3-CHLORO-PROPOXY)-6-METHOXY-QUINOLINE-3-CARBONITRILE plays a crucial role in the synthesis of Bosutinib, a targeted cancer therapy drug that inhibits the activity of certain enzymes involved in the development of cancer cells.
The application of 4-Chloro-7-(3-chloropropoxy)-6-methoxy-quinoline-3-carbonitrile in the pharmaceutical industry is primarily due to its utility in the production of Bosutinib, which is a valuable anti-cancer agent. Bosutinib is particularly effective against various types of cancer, including leukemia, and has been shown to improve patient outcomes when used in combination with other treatments. The use of this intermediate in the green synthesis process also highlights its importance in developing more environmentally friendly and sustainable methods for producing life-saving medications.

InChI:InChI=1/C14H12Cl2N2O2/c1-19-12-5-10-11(6-13(12)20-4-2-3-15)18-8-9(7-17)14(10)16/h5-6,8H,2-4H2,1H3

Upstream product

• 627-30-5 1-chloro-3-hydroxypropane 
• 263149-10-6 4-chloro-7-hydroxy-6-methoxyquinolin-3-carbonitrile 
• 214470-66-3 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 3535-27-1 methyl 4-isopropoxy-3-methoxybenzoate 
• 50413-53-1 methyl 2-amino-4-isopropoxy-5-methoxybenzoate 
• 948553-02-4 4-isopropoxy-5-methoxy-2-nitro-benzoic acid methyl ester 
• 741276-43-7 7-isopropyloxy-6-methoxy-4-chloroquinoline-3-carbonitrile 
• 319492-96-1 7-isopropyloxy-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile 
• 111627-40-8 methyl 4-(3-chloropropoxy)-3-methoxybenzoate 
• 214470-59-4 2-Amino-4-(3-chloro-propoxy)-5-methoxy-benzoic acid methyl ester 
• 214470-57-2 methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate 
• 109-70-6 1.3-chlorobromopropane 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 

Downstream Products

• 331662-94-3 7-(3-chloropropoxy)-4-[(2,4-dichlorophenyl)amino]-6-methoxy-3-quinolinecarbonitrile 
• 380844-49-5 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile 
• 863029-97-4 4-{3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]anilino}-7-(3-chloropropoxy)-6-methoxy-3-quinolinecarbonitrile 
• 380843-81-2 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(piperazin-1-yl)propoxy)quinoline-3-carbonitrile 
• 380843-75-4 bosutinib 

Relevant articles and documents

Bosutinib purification method

The invention provides a bosutinib purification method. The method includes the steps of firstly, dissolving crude bosutinib in an acetonitrile-water mixed solvent; secondly, optionally performing activated carbon decoloring, and filtering to obtain filtrate; thirdly, cooling, crystallizing, filtering, and drying to obtain purified bosutinib. The bosutinib purification method has the advantages that the method can replace a column chromatography purification method or a preparative chromatography purification method to remove impurities, which is hard to purify by a conventional crystallizingmethod, in the crude bosutinib, and the method is low in solvent use amount, simple in process, high in purification yield and product purity and beneficial to industrial production.

A kind of deuterium generation 3-cyano-quinoline compound, a pharmaceutically acceptable composition, preparation method and its use

Disclosed in the invention are a deuterated 3-cyano quinoline compound or pharmaceutically acceptable salts, solvates, prodrugs, stereoisomers, tautomers, polymorphic substances, metabolites etc., and a pharmaceutical composition containing such compounds, and the use of these compounds or compositions in the preparation of drugs for treating or preventing tumours, especially drugs such as protein kinase inhibitors. Compared with the prior art, the compounds of the present invention have the clear advantages of properties such as plasma drug concentration, half-life, clearance, microsomal stability, bioavailability or enzyme inhibition and the like, and thus can more effectively inhibit the activities of more than one protein kinase and/or inhibit the growth of tumuor cells.

A new and practical synthesis of bosutinib

New and improved synthetic route of bosutinib is described on a decagram scale. An intramolecular cyclization of 3-amino-2-(2-bromobenzoyl)-acrylonitrile (22) in K2CO3/DMF condition to form the key 3-cyano-4-hydroxyquinoline intermediate (13) is adopted as the key step. Bosutinib is obtained in 13.7% yield over ten steps and 98.9% purity (HPLC), which make it as a process of cost effective, environmentally friendly and feasible for scale-up operation.