N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide

Base Information

• Chemical Name: N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide
• CAS No.: 1315355-93-1
• Molecular Formula: C29H30F3N5O2
• Molecular Weight: 537.5760096
• DSSTox Substance ID: DTXSID60693497
• Wikidata: Q27087914
• Pharos Ligand ID: 75VYUVMZXH9F
• ChEMBL ID: CHEMBL4125960
• Mol file: 1315355-93-1.mol

Synonyms:N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-(1H-pyrrolo(2,3-b)pyridin-4-yloxy)benzamide;TAK1 inhibitor NG-25;TAK1 inhibitor NG25;transforming growth factor (TGF)-beta-activated kinase 1 (TAK1) inhibitor NG25

Chemical Property of N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide

Chemical Property:

• PKA: 12.91±0.70(Predicted)
• PSA: 76.98000
• Density: 1.313±0.06 g/cm3(Predicted)
• LogP: 6.33200
• Storage Temp.: 2-8°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 537.23515970
• Heavy Atom Count: 39
• Complexity: 808

Purity/Quality:

99% ^*data from raw suppliers

NG25 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCN(CC1)CC2=C(C=C(C=C2)NC(=O)C3=CC(=C(C=C3)C)OC4=C5C=CNC5=NC=C4)C(F)(F)F
• Uses: NG 25 inhibits TGF-beta-activated kinase 1 (TAK1). It also inhibits LYN, mitogen-activated protein kinase (MAP4K2) and Abl kinase activity.

Technology Process of N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide

There total 6 articles about N-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methyl-3-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzamide 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: 70.0%

N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)-phenyl)-4-methyl-3-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)benzamide → 3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide (1315355-93-1)

Guidance literature:

N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)-phenyl)-4-methyl-3-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)benzamide; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 5.5h;

In tetrahydrofuran; water; for 24h; Alkaline conditions;

DOI:10.1021/jm500480k

Reference yield:

3-hydroxy-4-methylbenzoic acid (586-30-1) → 3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide (1315355-93-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / dimethyl sulfoxide / 5 h / 100 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol

3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 5.5 h / 0 - 20 °C

4.2: 24 h / Alkaline conditions

With dmap; palladium 10% on activated carbon; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm500480k

Reference yield:

C21H25ClN2O4Si (1415564-64-5) → 3-((1H-pyrrolo[2,3-b]pyridin-4-yl)oxy)-N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide (1315355-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol

2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 5.5 h / 0 - 20 °C

3.2: 24 h / Alkaline conditions

With dmap; palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane;

DOI:10.1021/jm500480k

upstream raw materials:

6-chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

3-hydroxy-4-methylbenzoic acid

C₂₁H₂₅ClN₂O₄Si

Refernces

• 1、 -. "TYPE II RAF KINASE INHIBITORS". Page/Page column 73. . Retrieved 2011/08/08.