CPI-455

Base Information

• Chemical Name: CPI-455
• CAS No.: 1628208-23-0
• Molecular Formula: C16H14N4O
• Molecular Weight: 278.31
• Mol file: 1628208-23-0.mol

Synonyms:CPI-455;6-Isopropyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

Chemical Property of CPI-455

Chemical Property:

• Boiling Point: 488.7±55.0 °C(Predicted)
• PKA: -5.10±0.60(Predicted)
• PSA: 73.95000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 2.68468
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml)

Purity/Quality:

97% ^*data from raw suppliers

CPI-455 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: CPI-455 (1628208-23-0) is a potent (IC50?= 10 nM) and selective inhibitor of the lysine demethylase KDM5 (equal inhibition of KDM5A, 5B, 5C).1?CPI-455 reduced the number of drug-tolerant persister cancer cells (DTPs) in a dose-dependent, KDM5-dependent manner in multiple cell lines treated with standard chemotherapy or targeted agents. CPI-455 synergized with 5-aza-2’-deoxycytidine (DAC) to reduce the viability of luminal breast cancer cells?in vitro.2?KDM5 demethylases have recently been shown to repress the immune response to tumors?via?suppression of STING.3
• Uses: CPI-455 is a potent KDM5 demethylase inhibitor.

Technology Process of CPI-455

There total 4 articles about CPI-455 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: 42.0%

2-benzoyl-3-methyl-butyric acid ethyl ester (25491-47-8) + 3-amino-4-cyano-2H-pyrazole (16617-46-2) → 6-isopropyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (1628208-23-0)

Guidance literature:

With titanium tetrachloride; In 2-methyltetrahydrofuran; at 20 - 80 ℃; for 16.3333h;

Reference yield:

ethyl 3-oxo-3-phenylpropionate (94-02-0) → 6-isopropyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (1628208-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / 80 - 90 °C

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 23 °C

3: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 150 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; sodium carbonate; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2016.06.078

Reference yield:

7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (672323-30-7) → 6-isopropyl-7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (1628208-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 23 °C

2: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 150 °C

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; sodium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2016.06.078

upstream raw materials:

2-benzoyl-3-methyl-butyric acid ethyl ester

3-amino-4-cyano-2H-pyrazole

ethyl 3-oxo-3-phenylpropionate

7-oxo-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile