GSK5959

Base Information

• Chemical Name: GSK5959
• CAS No.: 901245-65-6
• Molecular Formula: C₂₂H₂₆N₄O₃
• Molecular Weight: 394.473
• Mol file: 901245-65-6.mol

Synonyms:GSK5959

Chemical Property of GSK5959

Chemical Property:

• Boiling Point: 527.3±50.0 °C(Predicted)
• PKA: 13.06±0.20(Predicted)
• PSA: 68.50000
• Density: 1.263±0.06 g/cm3(Predicted)
• LogP: 3.26620

Purity/Quality:

>98% ^*data from raw suppliers

GSK 5959 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GSK 5959 exhibits >100-fold selectivity for BRPF1 (IC50 = 80 nM) over a panel of 35 other bromodomains, including BRPF2/3 and BET family bromodomains. Inhibits BRPF1 interaction with histone H3.3, which is involved in the epigenetic regulation of gene expression and have been implicated in human cancer.
• Uses: GSK5959 is as elective BRPF1 bromodomain inhibitor.

Technology Process of GSK5959

There total 4 articles about GSK5959 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: 55.0%

5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazole-2(3H)-one (878432-74-7) + 2-Methoxybenzoyl chloride (21615-34-9) → N-(1,3-dimethyl-2-oxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-methoxybenzamide (901245-65-6)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/ml5002932

Reference yield:

5-fluoro-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one → N-(1,3-dimethyl-2-oxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-methoxybenzamide (901245-65-6)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic anhydride; nitric acid / 1 h / -30 - 0 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

3: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C / 760.05 Torr

4: pyridine / dichloromethane / 0.75 h / 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; nitric acid; acetic anhydride; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ml5002932

Reference yield:

5-fluoro-1,3-dimethyl-6-nitro-1,3-dihydro-2H-benzimidazol-2-one → N-(1,3-dimethyl-2-oxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-2-methoxybenzamide (901245-65-6)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 1 h / 120 °C / Inert atmosphere; Microwave irradiation

2: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 20 °C / 760.05 Torr

3: pyridine / dichloromethane / 0.75 h / 20 °C

With pyridine; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/ml5002932

upstream raw materials:

5-amino-1,3-dimethyl-6-(piperidin-1-yl)-1H-benzo[d]imidazole-2(3H)-one

2-Methoxybenzoyl chloride

Refernces

• 1、 Demont, Emmanuel H.,Bamborough, Paul,Chung, Chun-Wa,Craggs, Peter D.,Fallon, David,Gordon, Laurie J.,Grandi, Paola,Hobbs, Clare I.,Hussain, Jameed,Jones, Emma J.,Le Gall, Armelle,Michon, Anne-Marie,Mitchell, Darren J.,Prinjha, Rab K.,Roberts, Andy D.,Sheppard, Robert J.,Watson, Robert J.. "1,3-dimethyl benzimidazolones are potent, selective inhibitors of the brpf1 bromodomain". . p. 1190 - 1195. Retrieved 2015/04/27.