Defactinib

Base Information

• Chemical Name: Defactinib
• CAS No.: 1073154-85-4
• Molecular Formula: C20H21F3N8O3S
• Molecular Weight: 510.5
• Mol file: 1073154-85-4.mol

Synonyms:Defactinib;VS 6063;VS6063;VS-6063;Defactinib(PF-04554878);N-methyl-4-(4-((3-(N-methylmethan-3-ylsulfonamido)pyrazin-2-yl)methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzamide;N-methyl-4-((4-(((3-(N-methylmethylsulfonamido)pyrazin-2-yl)methyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzamide Defactinib(PF-04554878)(VS-6063);N-Methyl-4-[[4-[[[3-[methyl(methylsulfonyl)amino]-2-pyrazinyl]methyl]amino]-5-(trifluoromethyl)-2-pyrimidinyl]amino]benzamide

Chemical Property of Defactinib

Chemical Property:

• PKA: 15.16±0.46(Predicted)
• PSA: 153.71000
• Density: 1.495±0.06 g/cm3(Predicted)
• LogP: 3.36310
• Storage Temp.: -20°C (des.)
• Solubility.: Soluble in DMSO (up to at least 25mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

Defactinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Focal adhesion kinase (FAK) is a non-receptor tyrosine kinase that plays a vital role in many oncogenic pathways. Defactinib is a dose-dependent inhibitor of FAK, with maximal inhibition of FAK autophosphorylation in cells achieved at 10 μM. It is less effective against the related kinase PYK2. Defactinib restores the chemosensitivity of taxane-resistant cells to paclitaxel , although it is not cytotoxic alone. Defactinib decreases YB-1 phosphorylation and nuclear accumulation in an Akt-dependent manner. It is orally bioavailable, inhibiting FAK and augmenting paclitaxel action in suppressing the growth and number of ovarian cancer cell tumors in mice.
• Uses: Defactinib is a selective and orally active FAK inhibitor phase 2. Used in treating cancer patients as it decreases proliferation and increases apoptosis.

Technology Process of Defactinib

There total 2 articles about Defactinib 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: 78.0%

4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-methylbenzamide (1073160-19-6) + N-(3-aminomethyl-pyrazin-2-yl)-N-methyl-methane sulfonamide acetate → N-methyl-4-(4-((3-(N-methylmethan-3-ylsulfonamido)pyrazin-2-yl)methylamino)-5-(trifluoromethyl)pyrimidin-2-yl-amino)benzamide (1073154-85-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,1-dichloroethane; tert-butyl alcohol; at 80 ℃; for 9h;

Reference yield: 14.0%

4-amino-N-methyl-benzamide (6274-22-2) + N-(3-(((2-chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)methyl)pyrazin-2-yl)-N-methylmethanesulfonamide → N-methyl-4-(4-((3-(N-methylmethan-3-ylsulfonamido)pyrazin-2-yl)methylamino)-5-(trifluoromethyl)pyrimidin-2-yl-amino)benzamide (1073154-85-4)

Guidance literature:

With acetic acid; In butan-1-ol; at 100 ℃;

DOI:10.1016/j.chembiol.2021.01.003

Reference yield: 42.8%

N-methyl-4-(4-((3-(N-methylmethan-3-ylsulfonamido)pyrazin-2-yl)methylamino)-5-(trifluoromethyl)pyrimidin-2-yl-amino)benzamide (1073154-85-4) + di-tert-butyl dicarbonate (24424-99-5) → C35H45F3N8O9S

Guidance literature:

With dmap; In dichloromethane; at 45 ℃; for 24h; Reflux;

upstream raw materials:

4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-N-methylbenzamide

4-amino-N-methyl-benzamide

Refernces

• 1、 -. "SULFONYL AMIDE DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH". Page/Page column 53. . Retrieved 2009/04/24.