3-Amino-6-{4-[(4-Methylpiperazin-1-Yl)sulfonyl]phenyl}-N-Pyridin-3-Ylpyrazine-2-Carboxamide

Base Information

• Chemical Name: 3-Amino-6-{4-[(4-Methylpiperazin-1-Yl)sulfonyl]phenyl}-N-Pyridin-3-Ylpyrazine-2-Carboxamide
• CAS No.: 486424-20-8
• Molecular Formula: C21H23N7O3S
• Molecular Weight: 453.51700
• European Community (EC) Number: 690-692-6
• Wikidata: Q27074728
• Pharos Ligand ID: D981XMXS6AJ2
• ChEMBL ID: CHEMBL2177161
• Mol file: 486424-20-8.mol

Synonyms:AZD2858

Chemical Property of 3-Amino-6-{4-[(4-Methylpiperazin-1-Yl)sulfonyl]phenyl}-N-Pyridin-3-Ylpyrazine-2-Carboxamide

Chemical Property:

• PKA: 7.17±0.70(Predicted)
• PSA: 146.28000
• Density: 1.408±0.06 g/cm3(Predicted)
• LogP: 3.23100
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 453.15830879
• Heavy Atom Count: 32
• Complexity: 730

Purity/Quality:

99% ^*data from raw suppliers

AZD2858 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)S(=O)(=O)C2=CC=C(C=C2)C3=CN=C(C(=N3)C(=O)NC4=CN=CC=C4)N
• Description: AZD2858 is a selective GSK-3 inhibitor with an IC50 of 68 nM, activating Wnt signaling, increases bone mass in rats.
• Uses: AZD 2858 is a highly selective glycogen synthase kinase-3β (GSK3β) inhibitor used in the treatment of neurological diseases such as Alzheimer’s (1).

Technology Process of 3-Amino-6-{4-[(4-Methylpiperazin-1-Yl)sulfonyl]phenyl}-N-Pyridin-3-Ylpyrazine-2-Carboxamide

There total 5 articles about 3-Amino-6-{4-[(4-Methylpiperazin-1-Yl)sulfonyl]phenyl}-N-Pyridin-3-Ylpyrazine-2-Carboxamide 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: 79.0%

4-[(4-methylpiperazin-1-yl)sulfonyl]phenylboronic acid (486422-11-1) + 3-amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamide (486422-03-1) → AZD2858 (486424-20-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In ethanol; water; toluene; Inert atmosphere;

DOI:10.1021/jm201724m

Reference yield:

methyl 3-amino-6-bromopyrazine-2-carboxylate (6966-01-4) → AZD2858 (486424-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 4 h / 70 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / ethanol; water; toluene / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; water; toluene; 2: |Suzuki Coupling;

DOI:10.1021/jm201724m

Reference yield:

pyridin-3-ylamine (462-08-8) → AZD2858 (486424-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 4 h / 70 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / ethanol; water; toluene / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; water; toluene; 2: |Suzuki Coupling;

DOI:10.1021/jm201724m

upstream raw materials:

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

pyridin-3-ylamine

1-((4-bromophenyl)sulfonyl)-4-methylpiperazine

4-[(4-methylpiperazin-1-yl)sulfonyl]phenylboronic acid

Refernces