5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid

Base Information

• Chemical Name: 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid
• CAS No.: 163521-19-5
• Molecular Formula: C26H26N4O3
• Molecular Weight: 442.517
• UNII: 93K783WZV4
• DSSTox Substance ID: DTXSID70458579
• Mol file: 163521-19-5.mol

Synonyms:163521-19-5;5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid;Vilazodone Carboxylic acid;Vilazodone metabolite M10;93K783WZV4;5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxylic acid;2-Benzofurancarboxylic acid, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-;2-Benzofurancarboxylic acid, 5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-;5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-2-benzofurancarboxylic acid;5-[4-[4-(5-cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid;5-{4-[4-(5-Cyano-1H-indol-3-yl)butyl]piperazin-1-yl}-1-benzofuran-2-carboxylic acid;5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylic acid;UNII-93K783WZV4;SCHEMBL2162650;DTXSID70458579;BCP12355;CS-M1885;HY-I0177;MFCD09833264;1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carboxybenzofuran-5-yl)piperazine;AKOS016004184;CS-O-08433;CS-14419;FT-0705778;I11783;A882566;cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-2-Benzofurancarboxylic acid;5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylicacid

Chemical Property of 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid

Chemical Property:

• Melting Point: 189-192 °C
• Boiling Point: 717.9±60.0 °C(Predicted)
• PKA: 15.98±0.30(Predicted)
• PSA: 96.50000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 4.63178
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 442.20049070
• Heavy Atom Count: 33
• Complexity: 730

Purity/Quality:

99.5% ^*data from raw suppliers

VilazodoneCarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCCCC2=CNC3=C2C=C(C=C3)C#N)C4=CC5=C(C=C4)OC(=C5)C(=O)O
• Uses: Vilazodone Vilazodone Carboxylic Acid is the carboxylic acid impurity and an intermediate in the preparation of the antidepressant Vilazodone (V265000).

Technology Process of 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid

There total 7 articles about 5-(4-(4-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxylic acid 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:

ethyl 5-nitrobenzo[d]furan-2-carboxylate (69604-00-8) → 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylic acid (163521-19-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / H₂ / Raney Ni / methanol / 27 h / 28 °C

2: 27 percent / K₂CO₃ / butan-1-ol / 48 h / Heating

3: K₂CO₃; Et₃N / acetonitrile / 12 h / Heating

4: KOH / methanol / 3 h / Heating

With potassium hydroxide; hydrogen; potassium carbonate; triethylamine; nickel; In methanol; acetonitrile; butan-1-ol;

DOI:10.1021/jm040793q

Reference yield:

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester (163521-11-7) → 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylic acid (163521-19-5)

Guidance literature:

With potassium hydroxide; In methanol; for 3h; Heating;

DOI:10.1021/jm040793q

Reference yield:

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) → 5-{4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl}benzofuran-2-carboxylic acid (163521-19-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / isobutyl-AlCl₂ / CH₂Cl₂ / 15 - 30 °C

2: 26 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 2 h

3: K₂CO₃; Et₃N / acetonitrile / 12 h / Heating

4: KOH / methanol / 3 h / Heating

With potassium hydroxide; isobutylaluminum dichloride; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm040793q

upstream raw materials:

5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester

1H-indole-5-carbonitrile

ethyl 5-nitrobenzo[d]furan-2-carboxylate

ethyl 5-amino-1-benzofuran-2-carboxylate

Downstream raw materials:

vilazodone

Refernces