492444-39-0

Basic information

• Product Name: 3-Quinolinecarbonitrile,4-chloro-6-Methoxy-7-[3-(4-Methyl-1-piperazinyl)propoxy]-
• Synonyms: 3-Quinolinecarbonitrile,4-chloro-6-Methoxy-7-[3-(4-Methyl-1-piperazinyl)propoxy]-;Bosutinib Impurity 9;4-Chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline
• CAS NO: 492444-39-0
• Molecular Formula: C₁₉H₂₃ClN₄O₂
• Molecular Weight: 374.86452
• EINECS: -0
• Mol File: 492444-39-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 548.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 7.63±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3-Quinolinecarbonitrile,4-chloro-6-Methoxy-7-[3-(4-Methyl-1-piperazinyl)propoxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarbonitrile,4-chloro-6-Methoxy-7-[3-(4-Methyl-1-piperazinyl)propoxy]-(492444-39-0)
• EPA Substance Registry System: 3-Quinolinecarbonitrile,4-chloro-6-Methoxy-7-[3-(4-Methyl-1-piperazinyl)propoxy]-(492444-39-0)

Safety Data

• Hazardous Substances Data: 492444-39-0(Hazardous Substances Data)

Usage

Uses

4-Chloro-3-cyano-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline is a useful reagent to prepare?benzofuranyl derivatives for treating solid tumours. It is also an impurity of Bosutinib.

Upstream product

• 5317-33-9 3-(4-methyl-1-piperazinyl)-1-propanol 
• 263149-10-6 4-chloro-7-hydroxy-6-methoxyquinolin-3-carbonitrile 
• 109-01-3 1-methyl-piperazine 
• 214470-57-2 methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate 

Downstream Products

• 380843-75-4 bosutinib 

Relevant articles and documents

Preparation method of disubstituted 4-chloroquinoline-3-carbonitrile derivative and preparation method of bosutinib

The invention provides a preparation method of a disubstituted 4-chloroquinoline-3-carbonitrile derivative and a preparation method of bosutinib. The preparation method of the disubstituted 4-chloroquinoline-3-carbonitrile derivative comprises the following steps: disubstituted o-nitrobenzoate (II) used as a raw material and acetonitrile are condensed under the action of an alkali to obtain a compound of formula III; the compound of formula III and a chloroformylating reagent undergo a chloroformylating reaction to obtain a compound of formula IV1 or formula IV2; and the compound of formula IV1 undergoes catalytic hydrogenation cyclization in the presence of a hydrogenation catalyst to prepare 7-[3-(4-methyl-1-piperazinyl)propoxy]-6-methoxy-4-chloroquinoline-3-carbonitrile (Ia), or the compound of formula IV2 is subjected to catalytic hydrogenation cyclization and anhydride amidation to prepare 6-acetamido-7-ethoxy-4-chloroquinolin-3-carbonitrile (Ib). The compound of formula Ia or Ibis used to prepare bosutinib, neratinib or pelitinib. The method of the invention has the advantages of short process flow, simplicity in operation, easiness in realization, low cost, few three wastes, high yield, high purity, and easiness in industrial production.

Synthesis and structure-activity relationship of 4-(2-aryl-cyclopropylamino)-quinoline-3-carbonitriles as EGFR tyrosine kinase inhibitors

Synthesis and structure-activity relationship of a series of 4-(2-aryl-cyclopropylamino)-quinoline-3-carbonitrile derivatives as EGFR inhibitors is described. Compounds 29 and 30 showed potent in vitro inhibitory activity in the enzymatic assay as well as in the functional cellular assay. They are moderately selective against other types of tyrosine kinases.

SUBSTITUTED 3-CYANOQUINOLINES AS MEK INHIBITORS

The invention concerns quinoline derivatives of Formula (I) wherein each of Z1, m, R1, n, R3, Z2 and R14 have any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive or anti-proliferative agent in the containment and/or treatment of solid tumour disease.