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

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

Uses

Used in Pharmaceutical Research:
4-Chloro-6-acetoxy-7-methoxyquinazoline hydrochloride is used as a research compound for the development of drugs, particularly in the treatment of cancer and other diseases. Its specific properties and uses are not extensively documented, suggesting that it may play a role in niche research or specialized chemical applications within the pharmaceutical industry.

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF N-(3-ETHYNYLPHENYL)-7-METHOXY-6-(3-MORPHOLINOPROPOXY) QUINAZOLIN -4-AMINE DIHYDROCHLORIDE

Present invention relates to an improved process for the preparation of N-(3- ethynylphenyl)-7-methoxy-6-(3-morpholinopropoxy) quinazolin-4-amine dihydrochloride of formula-I.

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.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

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.

NOVEL AMIDE DERIVATIVE FOR INHIBITING THE GROWTH OF CANCER CELLS

The present invention provides a novel amide derivative and a pharmaceutically acceptable salt thereof which selectively and effectively inhibits the growth of cancer cells induced by the overexpression of an epidermal growth factor receptor and also prevents the development of drug resistance caused by the mutation of EGFR tyrosine kinase, and a pharmaceutical composition comprising same as an active ingredient.

Improved synthesis of substituted 6,7-dihydroxy-4-quinazolineamines: Tandutinib, erlotinib and gefitinib

The synthesis of three substituted 6,7-dihydroxy-4-quinazolineamines: tandutinib (1), erlotinib (2) and gefitinib (3) in improved yields is reported. The intermediates were characterized by NMR and the purities determined by HPLC.

Quinazoline compounds and pharmaceutical compositions containing them

The use of a compound of formula (I) or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, NH or NR8 where R8 is hydrogen or C1-6alkyl; Ra is a 3-quinoline group or a group of sub-formula (i) where R5, R6 and R7 are various specific organic groups, in the preparation of a medicament for use in the inhibtion of aurora 2 kinase. Novel compounds of formula (I) and pharmaceutical compositions useful in the treatment of cancer are also described and claimed.

QUINAZOLINE BASED PROTEIN KINASE INHIBITORS

Hydroxy containing quinazoline based derivatives have enhanced and unexpected drug properties as inhibitors of protein kinases and are useful in treating disorders related to abnormal protein kinase activities such as cancer.

Substituted anilino-quinazoline (or quinoline) compounds and use thereof

The invention concerns amide derivatives of Formula (I), wherein: G is N or CH; R1is a group such as hydroxy, halo, trifluoromethyl, C1-6alkyl and C1-6alkoxy; each of R2and R3is hydrogen, halo, C1-6alkyl, C2-6alkenyl or C2-6alkynyl; R4is a group such as hydrogen, hydroxy, C1-6alkyl, C1-6alkoxy and C3-7cycloalkyl, or R4is of the Formula (IC): —K—J, wherein J is aryl, heteroaryl or heterocyclyl and K is a bond or a group such as oxy and imino, R5is a group such as hydrogen, halo and trifluoromethyl: m is 1-3 and q is 0-4; or pharmaceutically acceptable salts or in vivo cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.