GSK-2256098

Base Information

• Chemical Name: GSK-2256098
• CAS No.: 1224887-10-8
• Molecular Formula: C₂₀H₂₃ClN₆O₂
• Molecular Weight: 414.895
• Mol file: 1224887-10-8.mol

Synonyms:2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N(methyloxy)benzamide

Chemical Property of GSK-2256098

Chemical Property:

• PKA: 5.24±0.10(Predicted)
• Density: 1.32±0.1 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

GSK2256098 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GSK2256098 is an inhibitor of focal adhesion kinase (FAK). It is selective for FAK, inhibiting only FAK greater than 50% in a panel of 261 kinases. GSK2256098 inhibits FAK autophosphorylation at tyrosine 397 (Y397) in OVCAR8 ovarian, U87MG glioblastoma, and A549 lung cancer cell lines (IC50s = 15, 8.5, and 12 nM, respectively). It induces apoptosis and increases PARP levels, decreases viability (IC50 = 25 μM), and inhibits colony formation in L3.6P1 cells. GSK2256098 (75 mg/kg per day) also leads to lower tumor weight and fewer metastases in the Ishikawa orthotopic mouse model of uterine cancer.
• Uses: GSK 2256098 is FAK inhibitor. It can be used in biological study of molecular pathways: endothelial cell FAK-?A target for cancer treatment.

Technology Process of GSK-2256098

There total 6 articles about GSK-2256098 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: 15.0%

2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (1201935-41-2) + 3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (1124-16-9) → 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N(methyloxy)benzamide (1224887-10-8)

Guidance literature:

With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; at 160 ℃; for 0.666667h; Microwave irradiation;

Reference yield:

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]benzoic acid (1224887-83-5) + N-methoxylamine hydrochloride (593-56-6) → 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N(methyloxy)benzamide (1224887-10-8)

Guidance literature:

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]benzoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 0.5h;

N-methoxylamine hydrochloride; In N,N-dimethyl-formamide; for 0.25h;

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

Reference yield:

2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile (1224887-80-2) → 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N(methyloxy)benzamide (1224887-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / Inert atmosphere; Reflux

2.1: sodium hydroxide; water / 1,4-dioxane / Reflux

3.1: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide / N,N-dimethyl-formamide / 0.5 h

3.2: 0 - 20 °C

With water; palladium diacetate; benzotriazol-1-ol; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium hydroxide; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide

3-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]benzoic acid

N-methoxylamine hydrochloride

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