179688-54-1

Basic information

• Product Name: 4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride
• Synonyms: 6-Quinazolinol, 4-chloro-7-methoxy-, 6-acetate, hydrochloride (1:1);4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride;4-Chloro-7-methoxyquinazolin-6-yl acetate monohydrochloride;4-Chloro-7-methoxyquinazolin-6-yl Acetate HCl;4-chloro-7-Methoxy-quinazolin-6-yl acetate hydrochloride;4-chloro-6- 7-methoxyquinazolin-6-yl acetate
• CAS NO: 179688-54-1
• Molecular Formula: C11H10Cl2N2O3
• Molecular Weight: 289.11
• Mol File: 179688-54-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 393.3 °C at 760 mmHg
• Flash Point: 191.6 °C
• Appearance: /
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride(179688-54-1)
• EPA Substance Registry System: 4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride(179688-54-1)

Safety Data

• Hazardous Substances Data: 179688-54-1(Hazardous Substances Data)

Usage

General Description

4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride is a chemical compound that comes under the class of quinazolines. This chemical has the molecular formula C11H10ClNO4.HCl. Considering its molecular structure, it contains atoms of chlorine, hydrogen, nitrogen, oxygen and also has an additional hydrogen chloride (HCl) unit. Quinazolines, like this particular compound, are often used in pharmaceutical research for developing drugs related to the treatment of cancer and other diseases. However, not much information is available regarding the specific properties or uses of this exact compound, pointing towards its possible role in niche research or specific chemical applications.

InChI:InChI=1/C11H9ClN2O3.ClH/c1-6(15)17-10-3-7-8(4-9(10)16-2)13-5-14-11(7)12;/h3-5H,1-2H3;1H

Upstream product

• 5653-40-7 2-Amino-4,5-dimethoxybenzoic acid 
• 7719-09-7 thionyl chloride 
• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 179688-53-0 7-methoxy-4-oxo-3,4-dihydroquinazolin-6-yl acetate 
• 179688-52-9 6-hydroxy-7-methoxyquinazolin-4(3H)-one 
• 13794-72-4 3H-6,7-dimethoxyquinazolin-4-one 

Downstream Products

• 1092365-53-1 N-(3-chloro-2,4-difluorophenyl)-7-methoxy-6-((3S)-pyrrolidin-3-yloxy)quinazolin-4-amine 
• 1092364-02-7 1-((3S)-3-(4-(3-chloro-2,4-difluorophenylamino)-7-methoxyquinazolin-6-yloxy)pyrrolidin-1-yl)pro-2-pen-1-one 
• 1012057-17-8 4-(3-ethynylphenylamino)-7-methoxyquinazolin-6-yl acetate hydrochloride 

Relevant articles and documents

INHIBITORS OF MUTANT EGFR FAMILY TYROSINE-KINASES

An epidermal growth factor receptor (EGFR) family tyrosine kinase inhibitor comprising a functional group that can bind to the serine S797 residue in EGFR having a C797S mutation or the serine S805 residue in HER2 having a C805S mutation.

Practical and efficient synthesis of gefitinib through selective O-alkylation: A novel concept for a transient protection group

A practical process that includes a simple four-step procedure for the preparation of gefitinib (1), a tyrosine kinase inhibitor that targets the epidermal growth factor receptor, is described. Dramatic improvements over previously reported conventional synthetic procedures were achieved. We found effective coupling conditions to minimize the inevitable production of an N-alkylated side product, N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholinopropoxy)-N-(3-morpholinopropyl)-quinazoline-4-amine (3) using a transient trimethylsilyl protecting group. We synthesized gefitinib in an 81.1% overall yield from a commercially available starting material on a multigram scale using a route that did not require work-up of any of the reaction steps.

Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives

A series of 6, 7-dialkoxy-4-anilinoquinazolines were designed, synthesized by substituting different heterocycles on 6-position and a variety of anilines on 4-position of the quinazoline. These novel quinazoline compounds were screened for their cytotoxic effect on epidermal growth factor receptor overexpressing skin epidermoid carcinoma cell line (A431), by using nonoverexpressing tumor cells as negative control (breast adeno carcinoma cell line MCF-7). 2-Butyl-4-chloro-1-{3-[7-methoxy-4-(3-(trifluoromethyl)phenylamino)quinazolin-6-yloxy]-propyl}-1H-imidazole-5-carboxaldehyde (30) and 2-butyl-4-chloro-1-{3-[4-(3-iodophenyl amino)-7-methoxyquinazolin-6-yloxy]propyl}-1H-imidazole-5-carboxaldehyde (33) were found to be more potent against A431 cell line (IC50 3.5 and 3 μM) and their activities are comparable to gefitinib. Insilico docking experiments with human EGFR Tyrosine kinase domain (PDB id-2gs2) indicated that 33 docks at the same position as that of gefitinib involving Val702, Ala719, Ser696, and Lys721.