5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde

Base Information

• Chemical Name: 5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde
• CAS No.: 231278-84-5
• Molecular Formula: C26H17ClFN3O3
• Molecular Weight: 473.891
• UNII: XA9X87F37H
• DSSTox Substance ID: DTXSID00457833
• Nikkaji Number: J1.696.961C
• Wikidata: Q72450744
• ChEMBL ID: CHEMBL3527095
• Mol file: 231278-84-5.mol

Synonyms:231278-84-5;5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde;5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde;5-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]quinazolin-6-yl]furan-2-carbaldehyde;Lapatinib metabolite M11;5-[4-[[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-6-quinazolinyl]-2-furancarboxaldehyde;XA9X87F37H;[5-[4-[4-[(3-Fluorobenzyl)oxy]-3-chloroanilino]-6-quinazolinyl]-2-furancarboxaldehyde;(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehyde;5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carboxaldehyde;5-(4-(3-Chloro-4-(3-fluorobenzyloxy)-anilino)-6-quinazolinyl)furan-2-carboxaldehyde;5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde;5-(4-(4-(3-fluorobenzyloxy)-3-chlorophenylamino)quinazolin-6-yl)furan-2-carbaldehyde;2-Furancarboxaldehyde, 5-(4-((3-chloro-4-((3-fluorophenyl)methoxy)phenyl)amino)-6-quinazolinyl)-;2-Furancarboxaldehyde, 5-[4-[[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-6-quinazolinyl]-;5-(4-((3-Chloro-4-((3-fluorophenyl)methoxy)phenyl)amino)-6-quinazolinyl)-2-furancarboxaldehyde;5-[4-({3-CHLORO-4-[(3-FLUOROPHENYL)METHOXY]PHENYL}AMINO)QUINAZOLIN-6-YL]FURAN-2-CARBALDEHYDE;C26H17ClFN3O3;5-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)-2-furaldehyde;5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde;5-(4-[3-Chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}furan-2-carbaldehyde;5-(4-{3-chloro-4-(3-fluorobenzyloxy)-anilino}-6-quinazolinyl)-furan-2-carbaldehyde;5-(4-{3-Chloro-4-[(3-fluorophenyl)methoxy]anilino}quinazolin-6-yl)furan-2-carbaldehyde;5-[4-[[3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl]amino]quinazolin-6-yl]furan-2-carboxaldehyde;5-{4-[3-Chloro-4-(3-fluorobenzyloxy)phenylamino]quinazolin-6-yl}furan-2-carbaldehyde;UNII-XA9X87F37H;SCHEMBL142106;CHEMBL3527095;DTXSID00457833;BCP22640;MFCD10565688;AKOS015888618;16,17-EPOXYPREGNENOLONEACETATE;AC-8335;SB18205;5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)-amino)quinazolin-6-yl)furan-2-carbaldehyde;AS-18220;AM20090639;C2786;CS-0100421;FT-0659647;F11830;A816574;Q-101358;5-(4-(4-(3-fluorobenzyloxy)-3-chloroanilino)-6-quinazolinyl)furan-2-formaldehyde;5-(4-{3-chloro-4-(3-fluorobenzyloxy)-anilino}-6-quinazol inyl)-furan-2-carbaldehyde;5-(4-{3-Chloro-4-[(3-fluorobenzyl)oxy]anilino}-6-quinazolinyl)-2-furaldehyde;5-[4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-quinazolin-6-yl]-2-furaldehyde;5-[4-({3-chloro-4-[(3-fluorobenzyl)oxy] phenyl}amino)quinazolin-6-yl]-2-furaldehyde;5-[4-({3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl} amino)quinazolin-6-yl]-2-furaldehyde;5-[4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]-6-quinazolinyl]furan-2-carboxaldehyde;5-[4-[3-Chloro-4-(3-fluorobenzyloxy)anilino]quinazoline-6-yl]furan-2-carbaldehyde;5-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-6-quinazolinyl]-2-furancarboxaldehyde;5-{-4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde;5-{4-[4-(3-fluoro-benzyloxy)-3-chloroanilino]-6-quinazolinyl}-2-furaldehyde;N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(5-formyl-2-furyl)-4-quinazolinamine;5-[4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl]-2-furaldehyde (Lapatinib Intermediate);5-[4-[[3-chloranyl-4-[(3-fluorophenyl)methoxy]phenyl]amino]quinazolin-6-yl]furan-2-carbaldehyde

Chemical Property of 5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde

Chemical Property:

• Vapor Pressure: 8.52E-17mmHg at 25°C
• Melting Point: 227.0 to 231.0 °C
• Refractive Index: 1.694
• Boiling Point: 650.3 °C at 760 mmHg
• PKA: 5.18±0.30(Predicted)
• Flash Point: 347.1 °C
• PSA: 77.25000
• Density: 1.407 g/cm³
• LogP: 6.89040
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 473.0942473
• Heavy Atom Count: 34
• Complexity: 675

Purity/Quality:

99% ^*data from raw suppliers

5-[4-[[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-6-quinazolinyl]-2-furancarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)F)COC2=C(C=C(C=C2)NC3=NC=NC4=C3C=C(C=C4)C5=CC=C(O5)C=O)Cl
• Uses: Lapatinib intermediate.

Technology Process of 5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde

There total 45 articles about 5-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)furan-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.7%

5-formylfurane-2-boronic acid (27329-70-0) + N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine (231278-20-9) → 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5)

Guidance literature:

With potassium carbonate; palladium diacetate; In tetrahydrofuran; ethanol; for 0.666667h; Product distribution / selectivity; Reflux;

Reference yield: 95.5%

5-formylfuran-2-boric acid + N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine (231278-20-9) → 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5)

Guidance literature:

With palladium 10% on activated carbon; triethylamine; In methanol; 1,2-dimethoxyethane; water; at 50 ℃; for 24h;

Reference yield: 95.0%

furfural (98-01-1) + N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine (231278-20-9) → 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5)

Guidance literature:

furfural; With n-butyllithium; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; hexane; at -20 ℃; for 1.25h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -15 ℃; for 0.25h;

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In tetrahydrofuran; ethanol; hexane; at 60 ℃;

DOI:10.1016/S0040-4020(02)00073-X

upstream raw materials:

furfural

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-iodoquinazolin-4-amine

5-formylfurane-2-boronic acid

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-iodoquinazolin-4-amine hydrochloride

Downstream raw materials:

lapatinib ditosylate

lapatanib

N-(3-chloro-4-(3-fluorobenzyloxy)phenyl)-6-(5-((2-(methylsulfonyl)ethylimino)methyl)furan-2-yl)quinazolin-4-amine

3-[5-{4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl}furan-2-yl]acrylic acid tert-butyl ester

Refernces

• 1、 -. "Preparation method of 6-substituted furanyl-4-substituted aminoquinazoline derivative and key intermediate thereof". . . Retrieved 2020/02/14.
• 2、 Zhang, Yaling,Chen, Li,Li, Xiabing,Gao, Li,Hao, Yunxia,Li, Baolin,Yan, Yaping. "Novel 4-arylaminoquinazolines bearing N,N-diethyl(aminoethyl)amino moiety with antitumour activity as EGFRwt-TK inhibitor". . p. 1668 - 1677. Retrieved 2019/10/14.