179688-52-9

Basic information

• Product Name: 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one
• Synonyms: 6-HYDROXY-7-METHOXY-3,4-DIHYDROQUINAZOLIN-4-ONE;6-Hydroxy-7-Methoxyquinazoline-4-One;6-hydydroxy-7-methoxyquinazoline-4-one;6-Hydroxy-7-methoxy-3H-quinazolin-4-one;7-METHOXYQUINAZOLINE-4,6-DIOL;4(3H)-Quinazolinone, 6-hydroxy-7-Methoxy-;Gefitinib interMediate III;6-Hydroxy-7-Methoxyquinazolin-4(1H)-one
• CAS NO: 179688-52-9
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 192.17
• EINECS: 1308068-626-2
• Product Categories: API intermediates
• Mol File: 179688-52-9.mol

Chemical Properties

• Melting Point: 293 °C
• Boiling Point: 503.319 °C at 760 mmHg
• Flash Point: 258.198 °C
• Appearance: /
• Density: 1.478 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.659
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.39±0.20(Predicted)
• CAS DataBase Reference: 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one(179688-52-9)
• EPA Substance Registry System: 6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one(179688-52-9)

Safety Data

• Hazardous Substances Data: 179688-52-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one is used as a reactant for the preparation of 4-anilinoquinazoline derivatives, which have demonstrated antitumor activities. These derivatives are valuable in the development of anticancer drugs targeting various types of cancer.
Used in Medicinal Chemistry Research:
6-Hydroxy-7-methoxy-3,4-dihydroquinazolin-4-one is also utilized as a reactant in the synthetic preparation of 2-arylbenzothiazoles, which are known as kinase inhibitors. Kinase inhibitors are important in the regulation of cellular processes and have potential applications in the treatment of various diseases, including cancer and inflammatory conditions.

InChI:InChI=1/C9H8N2O3/c1-14-8-3-6-5(2-7(8)12)9(13)11-4-10-6/h2-4,12H,1H3,(H,10,11,13)

Upstream product

• 63-68-3 L-methionine 
• 184475-71-6 4-(3-chloro-4-fluorophenylamino)-6-hydroxy-7-methoxyquinazoline 
• 50413-44-0 methyl 2-amino-5-hydroxy-4-methoxybenzoate 
• 16712-16-6 ammonium formate 
• 77287-34-4 formamide 
• 20323-74-4 2-carboethoxy-4,5-dimethoxyaniline 
• 100905-33-7 ethyl 2-nitro-4,5-dimethoxybenzoate 
• 3943-77-9 ethyl veratrate 
• 93-07-2 Veratric acid 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 3473-63-0 formamidine acetic acid 
• 31839-21-1 2-amino-5-hydroxy-4-methoxybenzoic acid 
• 463-52-5 formamidine 

Downstream Products

• 179688-53-0 6-acetoxy-7-methoxy-3,4-dihydroquinazolin-4-one 
• 808762-62-1 4-((4-bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate 
• 808762-63-2 4-((4-bromo-2-fluorophenyl)amino)-7-methoxyquinazolin-6-ol 
• 1437310-79-6 N-(4-bromo-2-fluorophenyl)-6-(3-chloropropoxy)-7-methoxyquinazolin-4-amine 
• 1438072-35-5 N-(4-bromo-2-fluorophenyl)-7-methoxy-6-(3-(tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrol-6(3H)-yl)propoxy)quinazolin-4-amine 
• 1438080-43-3 tert-butyl 5-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate 
• 1438072-41-3 N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)propoxy)-7-methoxyquinazolin-4-amine 
• 1438072-47-9 N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)propoxy)quinazolin-4-amine 
• 1438080-49-9 tert-butyl 1-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3.4-b]pyrrole-5(1H)carboxylate 
• 1438072-53-7 N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydropyrrolo[3.4-b]pyrrol-1(2H)-yl)propoxy)-7-methoxyquinazolin-4-amine 
• 1438072-59-3 1-(1-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)ethanone 
• 1438075-52-5 N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-(4-methylhexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl) propoxy)quinazolin-4-amine 
• 1438075-59-2 6-(3-(4-benzylhexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)propoxy)-N-(3-chloro-4-fluorophenyl)-7-methoxyquinazolin-4-amine 
• 1438081-00-5 tert-butyl 6-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)octahydro-1H-pyrrolo[2,3-c] pyridine-1-carboxylate 

Relevant articles and documents

Studies leading to the identification of ZD1839 (Iressa): An orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer

This paper describes the development of the epidermal growth factor receptor tyrosine kinase inhibitor ZD1839 from a lead series of 4-anilinoquinazoline compounds. ZD1839 has suitable properties for use as a clinically effective drug and shows activity against human tumours. In particular, the use of pharmacokinetic data in the development of ZD1839 is discussed.

Preparation method of novel anti-cancer drug AZD3759

The invention provides a preparation method of a novel anticancer drug AZD3759, and relates to the technical field of medicinal chemistry. The preparation method comprises the following steps: hydrolyzing 3, 4-dihydro-7-methoxy-4-oxoquinazolin-6-alcohol acetate to obtain a compound 2, by (R)-(-)-2-methylpiperazine as a raw material, carrying out nucleophilic addition-elimination to obtain a compound 4, carrying out chloroformylation on the compound 4 to obtain a compound 5, carrying out esterification reaction on the compound 2 and the compound 5 to obtain a compound 6, carrying out Boc removal reaction on the compound 6 to obtain a compound 7, carrying out methylation reaction on the compound 7 to obtain a compound 8, carrying out chlorination reaction on the compound 8 to obtain a compound 9, and finally, carrying out an alkylation reaction process on the compound 9 and 2-fluoro-3-chloroaniline so that AZD3759 is obtained. The preparation method provided by the invention has the advantages of cheap and accessible raw materials and lower cost, sodium cyanoborohydride is not used in the reaction process, so that the method is more environment-friendly, the product yield is high, and industrial large-scale production is facilitated.

Preparation method of high-purity gefitinib key intermediate

The invention belongs to the field of drug synthesis, and particularly relates to a preparation method of a high-purity gefitinib key intermediate 6-hydroxy-7-methoxy-3H-quinazoline-4-ketone. The synthesis method is simple to operate, the yield is high, t

Synthesis method of tumor cell inhibition drug

The invention relates to the technical field of organic synthesis and drugs, and discloses a synthesis method of a tumor cell inhibition drug. 3-hydroxy-4-methoxybenzaldehyde is taken as a starting raw material, aldehyde ortho-hydrogen is activated through a temporary guide group to facilitate amino substitution, [4 + 2] cyclization addition reaction is combined for cyclization, and introduction of a propyl morpholine side chain to a hydroxyl group, chlorination and introduction of a fluorochloroaniline side chain are sequentially carried out to finally prepare gefitinib. The synthesis path ofthe tumor cell inhibition drug gefitinib reduces reaction steps, shortens the reaction time, reduces the production cost, reduces the generation of impurities in the system, and reduces the emissionof three wastes.

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.

Preparation method of targeted drug AZD3759 intermediate

The invention discloses a preparation method of a targeted drug AZD3759 intermediate, which comprises the following steps of: firstly, 6-nitro veratric acid is hydrolyzed under alkaline conditions toobtain 2-nitro-4-methoxy-5-hydroxybenzoic acid, the 2-nitro-4-methoxy-5-hydroxybenzoic acid is then reduced by hydrazine hydrate under the action of catalyst ferric chloride hexahydrate activated carbon mixture to obtain 2-amino-4-methoxy-5-hydroxybenzoic acid, 2-amino-4-methoxy-5-hydroxybenzoic acid is reacted with formamidine acetate to obtain 4,6-dihydroxy-7-methoxyquinazoline, 4,6-dihydroxy-7-methoxyquinazoline is reacted with acetyl chloride under alkaline conditions to obtain 4-hydroxyl-6-acetoxy-7-methoxyquinazoline, finally 4-hydroxyl-6-acetoxy-7-methoxyquinazoline is reacted with 3-chlorine-2-fluoroaniline by Mitsunobu reaction under the action of triphenylphosphine and azo reagent to obtain 4-[(3-chloro-2-fluorophenyl)amino]-6-acetoxy-7-methoxyquinazoline. The invention reduces the synthesis steps, reduces the use of harmful compounds, reduces the production cost and optimizes the production operation.

A preparation method of gefitinib (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular relates to a preparation method of gefitinib. The present invention provides a preparation method of gefitinib, obtained by formula I compounds, the formula I compound preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. The present invention provides a preparation method can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)

A 3, 4 - dihydro -7 - methoxy -4 - [...] -6 - ethoxylate ester preparation method (by machine translation)

The present invention relates to organic chemical and medical technology field, in particular to a 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method. The present invention provides a gefitinib 3, 4 - dihydro - 7 - methoxy - 4 - [...] - 6 - ethoxylate ester preparation method comprises the following steps: nitration reaction, oxidation reaction, selective demethylation reaction, reduction reaction, a cyclization reaction, phenolic hydroxyl acetylation reaction. Preparation method provided by the invention can at the same time reducing the cost, it is easy for the refined purification, easy preparation and control of related impurities, the overall preparation process routes are greatly optimized, is suitable for industrial scale production. (by machine translation)

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.

EGFR PROTEOLYSIS TARGETING CHIMERIC MOLECULES AND ASSOCIATED METHODS OF USE

The present disclosure relates to bifunctional compounds, which find utility as modulators of receptor tyrosine kinase (RTK) proteins. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a ligand which binds to an E3 ubiquitin ligase and on the other end a moiety which binds a target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effectuate ubiquitination, and therefore, degradation (and inhibition) of the target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.