N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine

Base Information

• Chemical Name: N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine
• CAS No.: 153436-54-5
• Deprecated CAS: 197252-54-3,430475-82-4
• Molecular Formula: C16H15BrClN3O2
• Molecular Weight: 360.21
• Hs Code.: 2933990090
• European Community (EC) Number: 802-811-2
• UNII: TC62B68RSL
• DSSTox Substance ID: DTXSID80165328
• Nikkaji Number: J611.454G
• Wikidata: Q27163047
• Pharos Ligand ID: 742GHQSNPC1T
• ChEMBL ID: CHEMBL29197
• Mol file: 153436-54-5.mol

Synonyms:4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline;EBE-A22;N-(3-bromophenyl)-6,7-dimethoxy-4-quinazolinamine;PD 153035;PD-153035;PD153035

Chemical Property of N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine

Chemical Property:

• Vapor Pressure: 4.38E-09mmHg at 25°C
• Melting Point: 189-190 °C
• Refractive Index: 1.679
• Boiling Point: 472.1 °C at 760 mmHg
• PKA: 5.55±0.30(Predicted)
• Flash Point: 239.3 °C
• PSA: 56.27000
• Density: 1.499g/cm³
• LogP: 5.02810
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (up to 5 mg/ml).
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 359.02694
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

PD153035 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=CC=C3)Br)OC
• Description: AG-1517 HCl (153436-54-5) is an ultra-potent inhibitor of epidermal growth factor receptor tyrosine kinase (EGFR), with an IC50 of 25 pM. Inhibits other tyrosine kinases at micromolar or higher concentrations. It selectively blocks EGF-mediated cellular processes including mitogenesis, early gene expression and oncogenic transformation.1?Inhibits the growth of a number of cancer cell lines.2?AG-1517 HCl is an extremely useful tool for exploring EGF-mediated cellular signaling.3
• Uses: PD153035 is an inhibitor of EGFR, competitive with ATP. EGF Receptor: IC50 = 25 pM (Ki = 6 pM). PD 153035 is an extremely potent and specific inhibitor of EGFR tyrosine kinase activity.

Technology Process of N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine

There total 12 articles about N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine 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: 90.2%

N'-(2-cyano-4,5-dimethoxy-phenyl)-N,N-dimethyl-formamidine (385784-68-9) + m-Bromoaniline (591-19-5) → PD153035 (153436-54-5)

Guidance literature:

With acetic acid; for 3h; Reflux;

DOI:10.1016/j.tet.2013.12.028

Reference yield: 88.0%

m-Bromoaniline (591-19-5) + 6,7-dimethoxy-4-chloroquinazoline (13790-39-1) → PD153035 (153436-54-5)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 0.533333h; Microwave irradiation;

DOI:10.1016/j.tet.2009.11.091

Reference yield: 69.0%

(E)-N'-(2-cyano-4,5-dimethoxyphenyl)-N,N-dimethylformimidamide + m-Bromoaniline (591-19-5) → PD153035 (153436-54-5)

Guidance literature:

With acetic acid; In acetonitrile; at 160 ℃; for 0.166667h; microwave irradiation;

DOI:10.1021/ol047919y

upstream raw materials:

m-Bromoaniline

6,7-dimethoxy-4-chloroquinazoline

2-amino-4,5-dimethoxybenzonitrile

2-Amino-4,5-dimethoxybenzoic acid

Downstream raw materials:

4-(3-bromoanilino)-6,7-dihydroxyquinazoline

EBE-A₂₂

4-[(3-bromophenyl)amino]-6-hydroxy-7-methoxyquinazoline

Refernces

• 1、 Asquith, Christopher R.M.,Fleck, Neil,Torrice, Chad D.,Crona, Daniel J.,Grundner, Christoph,Zuercher, William J.. "Anti-tubercular activity of novel 4-anilinoquinolines and 4-anilinoquinazolines". . p. 2695 - 2699. Retrieved 2019/08/07.
• 2、 Juvale, Kapil,Gallus, Jennifer,Wiese, Michael. "Investigation of quinazolines as inhibitors of breast cancer resistance protein (ABCG2)". . p. 7858 - 7873. Retrieved 2014/01/06.