314771-88-5

Basic information

• Product Name: 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-
• Synonyms: 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-;(S)-N-(3-chloro-4-fluorophenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-aMine;7-((S)-tetrahydrofuran-3-yloxy)-4-(3-chloro-4-fluorophenyl)aMino-6-nitroquinazoline;N-(3-Chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-4-quinazolinaMine;Afatinib intermediate C;N-(3-Chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl];Afatinib Impurity 1;N-(3-chloro-4-fluorophenyl)-6-nitro-7-[(3S)-oxolan-3-yl]oxyquinazolin-4-amine
• CAS NO: 314771-88-5
• Molecular Formula: C18H14ClFN4O4
• Molecular Weight: 404.7795632
• EINECS: -0
• Product Categories: Afatinib Dimaleate
• Mol File: 314771-88-5.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 585.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.534±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.07±0.70(Predicted)
• CAS DataBase Reference: 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-(314771-88-5)
• EPA Substance Registry System: 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-(314771-88-5)

Safety Data

• Hazardous Substances Data: 314771-88-5(Hazardous Substances Data)

Usage

Description

4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]-, also known as (S)-N-(3-chloro-4-fluorophenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-amine, is a chemical compound that plays a crucial role in the synthesis of various pharmaceutical agents. It is characterized by its unique molecular structure, which includes a quinazoline core, a chloro-fluorophenyl group, a nitro group, and a tetrahydrofuranoxy group. 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]is known for its potential applications in the development of therapeutic agents, particularly in the field of oncology and respiratory diseases.

Uses

Used in Pharmaceutical Synthesis:
4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]is used as a key intermediate in the synthetic preparation of 4-anilinoquinazolines with C-6 urea-linked side chains. These synthesized compounds serve as inhibitors of the epidermal growth factor receptor (EGFR), which is a common target for cancer therapies. By inhibiting EGFR, these agents can help control the growth and proliferation of cancer cells.
Used in Oncology:
In the field of oncology, 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]is utilized in the preparation of (2Z)-Afatinib (A355305), a potent EGFR inhibitor. Afatinib is used for treating various types of cancer, including those of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder. By targeting the EGFR pathway, Afatinib can help slow down or stop the growth of cancer cells, providing a valuable treatment option for patients with these conditions.
Used in Respiratory Disease Treatment:
4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]also plays a role in the development of treatments for respiratory diseases. 4-QuinazolinaMine, N-(3-chloro-4-fluorophenyl)-6-nitro-7-[[(3S)-tetrahydro-3-furanyl]oxy]is involved in the synthesis of (2Z)-Afatinib, which has been found to be effective in managing conditions such as asthma and chronic obstructive pulmonary disease (COPD). By targeting the EGFR pathway, Afatinib can help reduce inflammation and improve lung function in patients with these respiratory disorders.

Upstream product

• 945553-94-6 N-((3-chloro-4-fluorophenyl)-6-nitro-7-phenylsulfonyl)quinazolin-4-one 
• 86087-23-2 (S)-3-hydroxytetyrahydrofurane 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 162012-67-1 N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine 
• 162012-70-6 4-chloro-7-fluoro-6-nitroquinazoline 
• 31374-18-2 7-chloro-3,4-dihydroquinazolin-4-one 
• 53449-14-2 7-chloro-6-nitro-4(3H)-quinazolinone 
• 162012-71-7 4,7-dichloro-6-nitro-quinazoline 
• 179552-73-9 7-chloro-N-(3-chloro-4-fluorophenyl)-6-nitroquinazolin-4-amine 
• 446-32-2 4-fluoroanthranilic acid 
• 16499-57-3 7-fluoro-3,4-dihydroquinazolin-4-one 
• 162012-69-3 7-fluoro-6-nitro-4-hydroxyquinazoline 
• 162012-69-3 7-fluoro-6-nitro-3H-quinazolin-4-one 
• 16499-57-3 7-fluoro-3H-quinazolin-4-one 

Relevant articles and documents

Design, synthesis and biological evaluation of novel 4-anlinoquinazoline derivatives as EGFR inhibitors with the potential to inhibit the gefitinib-resistant nonsmall cell lung cancers

A series of quinazoline derivatives with benzylidene hydrazine carboxamide were designed and synthesised as EGFR inhibitors. Most compounds exhibited exceptional anti-proliferative activity against A549, HepG2, MCF-7 and H1975 cells. Furthermore, six compounds demonstrated excellent inhibition activity against EGFRWT with the IC50 value both less than 2 nM. Among the six compounds, 44 exhibited the strongest activity (0.4 nM) and potently inhibited EGFRL858R/T790M (0.1 μM). Excitingly, the most potent compound 14 showed excellent enzyme inhibitory activity with 6.3 nM and 8.4 nM for both EGFRWT and EGFRT790M/L858R. The result of AO single staining and Annexin V/PI staining showed that the compound 14 and 44 could induce remarkable apoptosis of A549 cells. The compound 14 arrested the cell cycle at the S phase and compound 44 arrested the cell cycle at the G0 phase in A549 cells. These preliminary results demonstrate that compound 14 and 44 may be promising lead compound-targeting EGFR.

Afatinib refined product synthetic method

The invention discloses an afatinib refined product synthetic method, and belongs to the technical field of organic synthesis. The method particularly comprises the following steps that 4-fluoro-2-aminobenzoic acid and formamidine acetate are subjected to a ring-closure reaction to synthesize a compound of the formula I; the compound of the formula I is subjected to a nitration reaction to synthesize a compound of the formul II; the compound of the formula II and 3-chloro-4-fluoroaniline are subjected to dehydration to synthesize a compound of the formula III, the compound of the formula III and 3-hydroxy-tetrahydrofuran synthesize a compound of a formula IV through a nucleophilic substitution reaction; the compound of the formula IV is reduced to generate a compound of the formula V underthe Pd/C catalysis; the compound of the formula V and crotonic acid synthesizes a compound of the formula VI through a dehydration condensation reaction; the compound of the formula VI and dimethylamine finally synthesize the compound of the formula VII, that is to say, an afatinib refined product is obtained. According to the afatinib refined product synthetic method, the reaction process condition is mild, the corrosion risk to reaction equipment is lowered, the reaction process is simplified, operation is easy, the purity of the product is high, and the yield is increased conveniently.

4 - (Substituted phenylamino) aminoquin oxazolines, preparation method and application thereof

The invention specifically relates to novel 4-(substituted phenylamino)quinazoline compounds with antineoplastic activity and a preparation method thereof, belonging to the field of pharmaceutical chemical engineering. The 4-(substituted phenylamino)quinazoline compounds have an effective irreversible inhibiting effect on tyrosine kinase and/or good in-vivo pharmacokinetic behavior and are an effective tyrosine kinase irreversible inhibitor.