PF-562271 besylate

Base Information

• Chemical Name: PF-562271 besylate
• CAS No.: 939791-38-5
• Molecular Formula: C27H26F3N7O6S2
• Molecular Weight: 665.6638496
• UNII: FK2M84H8UI
• ChEMBL ID: CHEMBL2430359
• DSSTox Substance ID: DTXSID40240064
• NCI Thesaurus Code: C78199
• Mol file: 939791-38-5.mol

Synonyms:PF-00562271

Chemical Property of PF-562271 besylate

Chemical Property:

• PSA: 200.34000
• LogP: 6.51540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥11.1 mg/mL in DMSO with gentle warming
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 665.13380841
• Heavy Atom Count: 45
• Complexity: 1040

Purity/Quality:

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

PF562271Besylate ^*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.C1=CC=C(C=C1)S(=O)(=O)O
• Description: Focal adhesion kinase (FAK) and proline-rich tyrosine kinase 2 (PYK2) are non-receptor tyrosine kinases that constitute the FAK subfamily and play a vital role in many oncogenic pathways. PF-562271 is an ATP-competitive, reversible inhibitor of FAK (IC50 = 1.5 nM) that demonstrates 10-fold reduced potency for PYK2 (IC50 = 14 nM) and >100-fold selectivity against other protein kinases. PF-562271 inhibits FAK phosphorylation with an EC50 value of 93 ng/ml in glioblastoma-bearing mice and has been shown to regress tumors in multiple xenograft models.
• Uses: PF 562271 Besylate is the besylate salt of PF-562271, which is a potent, ATP-competitive, reversible inhibitor of focal adhesion kinase (FAK).

Technology Process of PF-562271 besylate

There total 5 articles about PF-562271 besylate 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: 82.0%

PF-562,271 (717907-75-0) + benzenesulfonic acid (98-11-3) → N-methyl-N-(3-((2-(2-oxoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)methanesulfonamide benzenesulfonate (939791-38-5)

Guidance literature:

In ethanol; water; at 70 ℃; Product distribution / selectivity; Industry scale;

Reference yield:

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → N-methyl-N-(3-((2-(2-oxoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)methanesulfonamide benzenesulfonate (939791-38-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zinc dibromide / 1,2-dichloro-ethane; tert-butyl alcohol / 0.5 h

1.2: 35 °C / Industry scale

2.1: diisopropylamine / isopropyl alcohol; toluene / 6.4 h / 10 - 90 °C / Industry scale

3.1: ethanol; water / 70 °C / Industry scale

With diisopropylamine; zinc dibromide; In ethanol; water; 1,2-dichloro-ethane; isopropyl alcohol; toluene; tert-butyl alcohol;

Reference yield:

5-trifluoromethyluracil (54-20-6) → N-methyl-N-(3-((2-(2-oxoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-ylamino)methyl)pyridin-2-yl)methanesulfonamide benzenesulfonate (939791-38-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; trichlorophosphate; phosphoric acid / water / 22 h / 20 - 100 °C / Industry scale

2.1: zinc dibromide / 1,2-dichloro-ethane; tert-butyl alcohol / 0.5 h

2.2: 35 °C / Industry scale

3.1: diisopropylamine / isopropyl alcohol; toluene / 6.4 h / 10 - 90 °C / Industry scale

4.1: ethanol; water / 70 °C / Industry scale

With phosphoric acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; trichlorophosphate; In ethanol; water; 1,2-dichloro-ethane; isopropyl alcohol; toluene; tert-butyl alcohol;

upstream raw materials:

PF-562,271

benzenesulfonic acid

2,4-dichloro-5-trifluoromethylpyrimidine

5-trifluoromethyluracil

Refernces