3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide

Base Information

• Chemical Name: 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide
• CAS No.: 1232410-49-9
• Molecular Formula: C18H16N4O3S
• Molecular Weight: 368.416
• Mol file: 1232410-49-9.mol

Synonyms:3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide;VE-821;3-amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide

Chemical Property of 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide

Chemical Property:

• Boiling Point: 568.4±50.0 °C(Predicted)
• PKA: 9.97±0.70(Predicted)
• PSA: 126.91000
• Density: 1.394
• LogP: 4.42760
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (40 mg/ml)

Purity/Quality:

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

VE 821 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Ataxia-telangiectasia and Rad3-related protein (ATR) is a serine/threonine kinase that activates DNA processes related to the DNA damage response. VE-821 is an ATP-competitive inhibitor of ATR (IC50 = 26 nM). It augments DNA damage and cell death of cancer cells in response to radiation under normal and hypoxic conditions. VE-821 also sensitizes cancer cells to chemotherapy.
• Uses: VE 821 is a potent and selective inhibitor of DNA damage response kinase, ATR. VE 821 functions to disrupt DNA damage repair system of tumor cells, limiting their abilities for further growth. VE-821 has been used as an inhibitor of ATM- and Rad3-related (ATR) protein in human cancer cells.

Technology Process of 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide

There total 6 articles about 3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide 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: 71.0%

3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylic acid (1232423-29-8) + aniline (62-53-3) → 3-amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide (1232410-49-9)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In 1,2-dimethoxyethane; at 120 ℃; for 18h;

Reference yield:

3-amino-6-bromo-N-phenyl-pyrazine-2-carboxamide (36204-92-9) → 3-amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide (1232410-49-9)

Guidance literature:

With sodium carbonate; In water; N,N-dimethyl-formamide; at 88 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jm101488z

Reference yield:

Methyl 3-amino-2-pyrazinecarboxylate (16298-03-6) → 3-amino-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide (1232410-49-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / acetonitrile / 18 h / 20 °C

2.1: lithium hydroxide / methanol; water / 2 h / Reflux

3.1: dmap; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 0.5 h

3.2: 18 h / 20 °C

4.1: sodium carbonate / water; N,N-dimethyl-formamide / 18 h / 88 °C / Inert atmosphere

With dmap; N-Bromosuccinimide; sodium carbonate; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; lithium hydroxide; In methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 4.1: Suzuki coupling;

DOI:10.1021/jm101488z

upstream raw materials:

3-amino-6-(4-(methylsulfonyl)phenyl)pyrazine-2-carboxylic acid

aniline

Methyl 3-amino-2-pyrazinecarboxylate

methyl 3-amino-6-bromopyrazine-2-carboxylate

Downstream raw materials:

3-hydroxy-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide

3-bromo-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide

3-methyl-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide

Refernces

• 1、 Charrier, Jean-Damien,Durrant, Steven J.,Golec, Julian M. C.,Kay, David P.,Knegtel, Ronald M. A.,MacCormick, Somhairle,Mortimore, Michael,O'Donnell, Michael E.,Pinder, Joanne L.,Reaper, Philip M.,Rutherford, Alistair P.,Wang, Paul S. H.,Young, Stephen C.,Pollard, John R.. "Discovery of Potent and Selective Inhibitors of Ataxia Telangiectasia Mutated and Rad3 Related (ATR) Protein Kinase as Potential Anticancer Agents". . p. 2320 - 2330. Retrieved 2011/06/17.