VE 822

Base Information

• Chemical Name: VE 822
• CAS No.: 1232416-25-9
• Molecular Formula: C24H25N5O3S
• Molecular Weight: 463.56
• Mol file: 1232416-25-9.mol

Synonyms:VX970; VE-822; VE 822

Chemical Property of VE 822

Chemical Property:

• Boiling Point: 674.4±55.0 °C(Predicted)
• PKA: 8.88±0.10(Predicted)
• PSA: 133.11000
• Density: 1.263±0.06 g/cm3(Predicted)
• LogP: 5.35110
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

3-[3-[4-[(Methylamino)methyl]phenyl]-5-isoxazolyl]-5-[4-[(1-methylethyl)sulfonyl]phenyl]-2-pyrazinamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-[3-[4-[(Methylamino)methyl]phenyl]-5-isoxazolyl]-5-[4-[(1-methylethyl)sulfonyl]phenyl]-2-pyrazinamine is a novel ATR (ATM-Rad3-related) inhibitor for in vitro and in vivo radiosensatization.

Technology Process of VE 822

There total 10 articles about VE 822 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:

C34H41N5O7S → 3-(3-{4-[(methylamino)methyl]phenyl}-1,2-oxazol-5-yl)-5-[4-(propan-2-ylsulfonyl)phenyl]pyrazin-2-amine (1232416-25-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/acs.jmedchem.9b00426

Reference yield:

N,N-di(tert-butoxycarbonyl)-5-(4-(isopropylsulfonyl)phenyl)-3-(3-(4-methyl)phenylisoxazol-5-yl)pyrazin-2-amine → 3-(3-{4-[(methylamino)methyl]phenyl}-1,2-oxazol-5-yl)-5-[4-(propan-2-ylsulfonyl)phenyl]pyrazin-2-amine (1232416-25-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 1 h / 85 °C

2: ethanol; dichloromethane / 1 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trifluoroacetic acid; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/acs.jmedchem.9b00426

Reference yield:

5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine (1349151-81-0) → 3-(3-{4-[(methylamino)methyl]phenyl}-1,2-oxazol-5-yl)-5-[4-(propan-2-ylsulfonyl)phenyl]pyrazin-2-amine (1232416-25-9)

Guidance literature:

Multi-step reaction with 8 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

3: dmap; triethylamine / dichloromethane / 18 h / 20 °C

4: sodium carbonate / methanol / 1 h / 20 °C

5: triethylamine / tetrahydrofuran / 20 - 60 °C

6: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / ethyl acetate / 1 h / 85 °C

7: ethanol; dichloromethane / 1 h / 20 °C

8: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With dmap; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); sodium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/acs.jmedchem.9b00426

upstream raw materials:

5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

3-bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-amine

tert-butyl N-tert-butoxycarbonyl-N-[5-(4-isopropylsulfonylphenyl)-3-(2-trimethylsilylethynyl)pyrazin-2-yl]carbamate

Refernces