N-(2,4-Difluorophenyl)-N'-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-fluorophenyl]urea

Base Information

• Chemical Name: N-(2,4-Difluorophenyl)-N'-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-fluorophenyl]urea
• CAS No.: 228559-41-9
• Molecular Formula: C24H18F3N3O4
• Molecular Weight: 469.41
• UNII: RP6UGT29FF
• ChEMBL ID: CHEMBL178455
• DSSTox Substance ID: DTXSID60462145
• Nikkaji Number: J2.885.475G
• Pharos Ligand ID: 3WYJSTLPHT3C
• Wikidata: Q27164581
• Mol file: 228559-41-9.mol

Synonyms:Ki 8751;Ki-8751;Ki8751;N-(2,4-difluorophenyl)-N'-(4-((6,7-dimethoxy-4-quinolyl)oxy)-2-fluorophenyl)urea

Chemical Property of N-(2,4-Difluorophenyl)-N'-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-fluorophenyl]urea

Chemical Property:

• Vapor Pressure: 5.12E-10mmHg at 25°C
• Melting Point: 239℃
• Refractive Index: 1.656
• Boiling Point: 497.1 °C at 760 mmHg
• Flash Point: 254.4 °C
• PSA: 81.71000
• Density: 1.429 g/cm³
• LogP: 6.25160
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (15 mg/ml)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 469.12494055
• Heavy Atom Count: 34
• Complexity: 677

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ki 8751 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-38
• Safety Statements: 37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=CN=C2C=C1OC)OC3=CC(=C(C=C3)NC(=O)NC4=C(C=C(C=C4)F)F)F
• Description: Ki8751 (228559-41-9) is a very potent (IC50 = 0.9 nM) inhibitor of vascular endothelial growth factor receptor 2 (VEGFR-2).1 It also inhibited PDGFRα (IC50 = 67 nM), c-Kit (IC50 = 40 nM), and FGFR2 (IC50 = 170 nM). Ki8751 completely suppressed HUVEC growth at 1 nM. Ki8751 completely inhibited tumor growth in LC-6 human tumor xenografts @ 5mg/kg. Ki8751 displayed anti-influenza A and B activity via disruption of virus entry in a PDGFR?/GM3-dependent manner.2
• Uses: Ki8751 is a potent and selective inhibitor of VEGFR2, PDGFRα and c-Kit with IC50 of 0.9 nM, 67 nM and 40 nM, respectively. KI 8751 is a potent and selective inhibitor of VEGFR-2-tyrosine kinase which inhibits proliferation of human umbilical vein endothelial cells and inhibits tumor growth.

Technology Process of N-(2,4-Difluorophenyl)-N'-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-fluorophenyl]urea

There total 5 articles about N-(2,4-Difluorophenyl)-N'-[4-[(6,7-dimethoxy-4-quinolinyl)oxy]-2-fluorophenyl]urea 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: 84.0%

2,4-diflurophenylisocyanate (59025-55-7) + 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (228559-74-8) → Ki 8751 (228559-41-9)

Guidance literature:

In toluene; for 0.5h; Heating;

DOI:10.1021/jm030427r

Reference yield:

2-amino-4,5-dimethoxyacetophenone (4101-30-8) → Ki 8751 (228559-41-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOMe / 1,2-dimethoxy-ethane / 1.17 h / 20 °C

1.2: 95 percent / 1,2-dimethoxy-ethane / 2 h / 20 °C

2.1: POCl₃ / Heating

3.1: 90 percent / chlorobenzene / 10 h / Heating

4.1: 91 percent / Zn; NH₄Cl / methanol / 10 h / Heating

5.1: 84 percent / toluene / 0.5 h / Heating

With sodium methylate; ammonium chloride; zinc; trichlorophosphate; In methanol; 1,2-dimethoxyethane; chlorobenzene; toluene;

DOI:10.1021/jm030427r

Reference yield:

6,7-dimethoxy-4-chloroquinoline (35654-56-9) → Ki 8751 (228559-41-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / chlorobenzene / 10 h / Heating

2: 91 percent / Zn; NH₄Cl / methanol / 10 h / Heating

3: 84 percent / toluene / 0.5 h / Heating

With ammonium chloride; zinc; In methanol; chlorobenzene; toluene;

DOI:10.1021/jm030427r

upstream raw materials:

2,4-diflurophenylisocyanate

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

6,7-dimethoxy-4-chloroquinoline

2-amino-4,5-dimethoxyacetophenone

Refernces