231278-20-9

Basic information

• Product Name: N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine
• Synonyms: N-[3-Chloro-4-(3-fluorobenzyloxy)-phenyl]-6-iodoquinazolin-4-amine;N-{3-Chloro-4-[(3-fluorophenyl)-methoxy]-phenyl}-6-iodo-4-quinazolinamine;6-Iodo-4-[3-chloro-4-(3-fluorobenzyloxy)anilino]quinazoline;N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-iodo-4-quinazolinamine;Lapatinib Intermediate 2;[3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl](6-iodoquinazol;N-{3-chloro-4-[(3-fluorophenyl)Methoxy]phenyl}-6-iodoquinazolin-4-aMine;4-[3-Chloro-4-(3-fluorobenzyloxy)phenylaMino]-6-iodoquinazoline, 97%
• CAS NO: 231278-20-9
• Molecular Formula: C₂₁H₁₄ClFIN₃O
• Molecular Weight: 505.71
• EINECS: 1806241-263-5
• Product Categories: Various Intermediates;Intermediate of lapatinib ditosylate;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Pharmaceutical intermediate;Lapatinib
• Mol File: 231278-20-9.mol
• Article Data: 34

Chemical Properties

• Melting Point: 222-224°C
• Boiling Point: 581.326 °C at 760 mmHg
• Flash Point: 305.375 °C
• Appearance: yellow solid
• Density: 1.691 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 5.04±0.50(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine(231278-20-9)
• EPA Substance Registry System: N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine(231278-20-9)

Safety Data

• Hazardous Substances Data: 231278-20-9(Hazardous Substances Data)

Usage

Description

N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine is a quinazoline derivative with a complex chemical structure, characterized by a yellow solid appearance. It has been utilized in the design, synthesis, and biological evaluation of quinazoline-phosphoramidate mustard conjugates, showcasing its potential as a pharmaceutical candidate for various applications.

Uses

Used in Pharmaceutical Industry:
N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine is used as a Lapatinib intermediate for the development of pharmaceutical compounds. Its unique chemical structure allows it to serve as a crucial building block in the synthesis of more complex molecules with potential therapeutic applications.
Used in Organic Chemical Synthesis:
N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine is used as an organic chemical synthesis intermediate, playing a vital role in the creation of various organic compounds. Its versatile structure enables it to be a key component in the development of new molecules with diverse applications in the chemical and pharmaceutical industries.
Used in Anticancer Drug Development:
N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine has been employed in the design, synthesis, and biological evaluation of quinazoline-phosphoramidate mustard conjugates as anticancer drugs. Its potential in this application is attributed to its ability to interact with specific biological targets, thereby exhibiting inhibitory effects on tumor growth and progression.

InChI:InChI=1/C21H14ClFIN3O/c22-18-10-16(5-7-20(18)28-11-13-2-1-3-14(23)8-13)27-21-17-9-15(24)4-6-19(17)25-12-26-21/h1-10,12H,11H2,(H,25,26,27)

Upstream product

• 98556-31-1 4-chloro-6-iodoquinazoline 
• 202197-26-0 3-chloro-4-(3-fluorobenzyloxy)aniline 
• 202197-25-9 {4-[(3-fluorobenzyl)oxy]phenyl}amine 
• 1227853-05-5 N⁽¹⁾-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-N,N-dimethylformamidine 
• 132131-24-9 5-iodoanthranilonitrile 
• 16064-08-7 6-iodo-1H-quinazolin-4-one 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 456-47-3 3-fluoro-benzenemethanol 
• 5326-47-6 2-amino-5-iodobenzoic acid 
• 443882-99-3 3-chloro-4-(3-fluorobenzyloxy)nitrobenzene 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 619-08-9 2-chloro-4-nitrophenol 
• 16064-08-7 6-iodo-4-hydroxyquinazoline 
• 944483-37-8 3-chloro-4-(3-fluoro-benzyloxy)-phenylamine hydrochloride 

Downstream Products

• 231278-84-5 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde 
• 320337-22-2 N-((4-(3-fluorobenzyloxy)-chlorophenyl)-6-(1-ethoxyethenyl)-quinazolin-4-yl)-amine 
• 320337-48-2 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(5-hydroxymethylfuran-2-yl)quinazoline 
• 231277-92-2 lapatanib 
• 443883-09-8 N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-(6-(2-bromoethanone)-quinazolin-4-yl)-amine 
• 388082-81-3 (4-(3-fluoro-benzyloxy)-3-chlorophenyl)-(6-(2-((2-methanesulphonyl-ethylamino)methyl)-thiazol-4-yl)-quinazolin-4-yl)-amine 
• 443883-07-6 N-{4-[(3-fluorobenzyloxy)]-chlorophenyl}-6-[2-({[2-(methanesulphonyl)ethyl]-[trifluoroacetyl]amino}methyl)-1,3-thiazol-4-yl]-(quinazolin-4-yl)-amine 
• 388082-75-5 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde 4-methylbenzenesulfonate 
• 1257665-55-6 3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]acrylic acid tert-butyl ester 
• 1152131-76-4 3-[5-{4-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}thiophene-2-yl] acrylic acid tert-butyl ester 
• 1257665-57-8 3-[3-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}phenyl]acrylic acid tert-butyl ester 
• 1152131-78-6 3-[4-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}phenyl]acrylic acid tert-butyl ester 
• 1152131-79-7 3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]acrylic acid 

Relevant articles and documents

Novel 4-arylaminoquinazolines bearing N,N-diethyl(aminoethyl)amino moiety with antitumour activity as EGFRwt-TK inhibitor

Herein, four novel 4-arylaminoquinazoline derivatives with N,N-diethyl(aminoethyl)amino moiety were designed, synthesised and evaluated on biological activities in vitro. All synthesised compounds have inhibitory effects against tumour cells (SW480, A549, A431 and NCI-H1975). In particular, 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(5-((N,N-diethyl(aminoethyl))aminomethyl)furan-2-yl)quinazoline (6a) and 6-(5-((N,N-diethylethyl)aminomethyl)furan-2-yl)-4-(4-(E)-(propen-1-yl)phenylamino)quinazoline (6d) were potent antitumour agents which showed high antiproliferative activities against tumour cells in vitro. Moreover, compound 6a could induce late apoptosis of A549 cells at high concentrations and arrest cell cycle of A549 cells in the G0/G1 phase at tested concentrations. Also, compound 6a could inhibit the activity of wild type epidermal growth factor receptor tyrosine kinase (EGFRwt-TK) with IC50 value of 15.60 nM. Molecular docking showed that compound 6a formed three hydrogen bonds with EGFRwt-TK, while lapatinib formed only two hydrogen bonds with the receptor protein. It is believed that this work would be giving a reference for developing anti-cancer drugs targeted EGFR-TK.

Preparation methods of tyrosine kinase inhibitor of Lapatinib and key intermediate of Lapatinib

The invention discloses preparation methods of a tyrosine kinase inhibitor of Lapatinib and a key intermediate of the Lapatinib, and belongs to the field of pharmaceutical and chemical industry. The preparation method of the Lapatinib intermediate uses a

Compounds capable of inhibiting ErbB/HDAC and preparation method thereof, and pharmaceutical composition comprising compounds and application thereof

The invention relates to compounds capable of inhibiting ErbB/HDAC and a preparation method thereof, and a pharmaceutical composition comprising the compounds and application thereof. The compounds are disclosed as Formula 1. The compounds or pharmaceutically acceptable salts, solvates, esters, acids, metabolites or prodrugs thereof, or the pharmaceutical composition comprising the compounds can be used for preparing ErbB kinases and HDAC activity inhibitors and also preparing ErbB-kinase/HDAC-activated mediated disease curatives.