PF-00562271 free base

Base Information

• Chemical Name: PF-00562271 free base
• CAS No.: 717907-75-0
• Molecular Formula: C₂₁H₂₀F₃N₇O₃S
• Molecular Weight: 507.496
• UNII: K5BX8ZA7UF
• ChEMBL ID: CHEMBL1084546
• DSSTox Substance ID: DTXSID10471000
• Nikkaji Number: J3.654.805C
• Pharos Ligand ID: BV5QLC6D4BH2
• Wikidata: Q27163236
• Mol file: 717907-75-0.mol

Synonyms:N-methyl-N-(3-(((2-((2-oxo-1,3-dihydroindol-5-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)methyl)pyridin-2-yl)methanesulfonamide;PF-562271;PF562271

Chemical Property of PF-00562271 free base

Chemical Property:

• PKA: 13.66±0.20(Predicted)
• PSA: 137.59000
• Density: 1.54 g/cm³
• LogP: 4.50130
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 507.13004319
• Heavy Atom Count: 35
• Complexity: 856

Purity/Quality:

99.0%, ^*data from raw suppliers

PF 562271 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C1=C(C=CC=N1)CNC2=NC(=NC=C2C(F)(F)F)NC3=CC4=C(C=C3)NC(=O)C4)S(=O)(=O)C
• Description: PF-562271 is a potent, ATP-competitive, reversible inhibitor of FAK with IC50 of 1.5 nM in cell-free assays, ~10-fold less potent for Pyk2 than FAK and >100-fold selectivity against other protein kinases, except for some CDKs.
• Uses: A potent, ATP-competitive and reversible inhibitor of FAK and Pyk2 catalytic activity with IC50s of 1.5 nM and 14 nM, respectively. PF-56227 is a potent, ATP-competitive, reversible inhibitor of focal adhesion kinase (FAK). Potent FAK inhibitor.

Technology Process of PF-00562271 free base

There total 6 articles about PF-00562271 free base 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: 68.3%

5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2,3-dihydro-1H-indol-2-one (717907-76-1) + N-(3-Aminomethyl-2-pyridyl)-N-methylmethanesulfonamide diacetate → PF-562,271 (717907-75-0)

Guidance literature:

With diisopropylamine; In isopropyl alcohol; toluene; at 10 - 90 ℃; for 6.4h; Industry scale;

Reference yield: 36.0%

5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2,3-dihydro-1H-indol-2-one (717907-76-1) + N-(3-aminomethyl-pyridin-2-yl)-N-methyl-methanesulfonamide dihydrochloride → PF-562,271 (717907-75-0)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 85 ℃;

DOI:10.1016/j.chembiol.2021.01.003

Reference yield:

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → PF-562,271 (717907-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) chloride / tert-butyl alcohol; dichloromethane

2: sodium carbonate / N,N-dimethyl-formamide / 85 °C

With sodium carbonate; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.chembiol.2021.01.003

upstream raw materials:

5-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-2,3-dihydro-1H-indol-2-one

5-trifluoromethyluracil

2,4-dichloro-5-trifluoromethylpyrimidine

5-amino-1,3-dihydro-2H-indol-2-one

Refernces

• 1、 -. "PYRIMIDINE DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH". Page/Page column 8. . Retrieved 2011/02/26.