Linifanib (ABT-869)

Base Information

• Chemical Name: Linifanib (ABT-869)
• CAS No.: 796967-16-3
• Molecular Formula: C21H18FN5O
• Molecular Weight: 375.405
• Hs Code.: 2933998090
• Mol file: 796967-16-3.mol

Synonyms:N-[4-(3-Amino-1H-indazol-4-yl)phenyl]-N'-(2-fluoro-5-methylphenyl)urea;ABT 869;

Chemical Property of Linifanib (ABT-869)

Chemical Property:

• Appearance/Colour: Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 180-183 °C (dec.)
• Refractive Index: 1.766
• Boiling Point: 542.203 °C at 760 mmHg
• PKA: 13.30±0.70(Predicted)
• Flash Point: 281.715 °C
• PSA: 95.83000
• Density: 1.424 g/cm³
• LogP: 5.63080
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO, Methanol

Purity/Quality:

Linifanib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Linifanib (ABT-869) is a novel, potent ATP-competitive RTK inhibitor for KDR, CSF-1R, Flt-1, Flt-3 and PDGFRβ with IC50 of 4 nM, 3 nM, 3 nM, 3 nM, and 66 nM respectively. Linifanib (ABT 869) is an oral tyrosine kinase inhibitor with antineoplasic activity. As a dual inhibitor, Linifanib, is being tested on several different cancers. An oral tyrosine kinase inhibitor with antineoplasic activity.

Technology Process of Linifanib (ABT-869)

There total 10 articles about Linifanib (ABT-869) 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%

N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea (796967-18-5) + 3-amino-4-chloro-1H-indazole (20925-60-4) → linifanib (796967-16-3)

Guidance literature:

With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate; In ethanol; water; at 55 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/op900208y

Reference yield: 74.8%

4-iodine-1H-indazol-3-ylamine (599191-73-8) + N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea (796967-18-5) → linifanib (796967-16-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In ethanol; for 8h; Reflux;

Reference yield:

3-amino-4-fluorotoluene (452-84-6) → linifanib (796967-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0 - 20 °C

2: Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / 1,2-dimethoxy-ethane; H₂O / 16 h / 85 °C

With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; dichloromethane; water; 2: Suzuki coupling;

DOI:10.1021/jm061280h

upstream raw materials:

4-iodine-1H-indazol-3-ylamine

N-(2-fluoro-5-methylphenyl)-N'-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]urea

3-amino-4-fluorotoluene

2-fluoro-6-iodobenzonitrile

Refernces

• 1、 Marlow, Maria,Al-Ameedee, Mohammed,Smith, Thomas,Wheeler, Simon,Stocks, Michael J.. "Linifanib-a multi-targeted receptor tyrosine kinase inhibitor and a low molecular weight gelator". . p. 6384 - 6387. Retrieved 2015/04/14.
• 2、 -. "CRYSTALLINE CHEMOTHERAPEUTIC". Page/Page column 13. . Retrieved 2009/05/28.