163521-20-8

Basic information

• Product Name: Vilazodone
• Synonyms: Ethyl 5-(piperazin-1-yl)benzofuran-2-carboxylate;Vilazodone Key interMediates;2-Benzofurancarboxylic acid,5-(1-piperazinyl)-,ethyl ester;5-(1-piperazinyl)benzofuran-2-carboxylic acid ethyl ester;5-(1-Piperazinyl)-2-benzofurancarboxylic Acid Ethyl Ester;Eehyl 5-(piperazin-1-yl)benzofuran-2-carboxylate;Ethyl 5-(PiperaziN-1-Yl-1-BenzofuraN-2-Carboxylate
• CAS NO: 163521-20-8
• Molecular Formula: C15H18N2O3
• Molecular Weight: 274.32
• EINECS: 1806241-263-5
• Mol File: 163521-20-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 429 °C at 760 mmHg
• Flash Point: 213.3 °C
• Appearance: /
• Density: 1.197 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO, Methanol
• PKA: 8.85±0.10(Predicted)
• CAS DataBase Reference: Vilazodone(CAS DataBase Reference)
• NIST Chemistry Reference: Vilazodone(163521-20-8)
• EPA Substance Registry System: Vilazodone(163521-20-8)

Safety Data

• Hazardous Substances Data: 163521-20-8(Hazardous Substances Data)

Usage

Uses

5-(1-Piperazinyl)-2-benzofurancarboxylic Acid Ethyl Ester is used in the synthesis of benzofuran derivatives for mycobacterium tuberculosis DNA GyrB inhibition.

Upstream product

• 64-17-5 ethanol 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 174775-48-5 ethyl 5-amino-1-benzofuran-2-carboxylate 
• 2725-81-7 6-nitrocoumarin 
• 10242-12-3 5-nitrobenzofuran-2-carboxylic acid 
• 50396-49-1 3-(2-hydroxy-5-nitrophenyl)acrylic acid 
• 56621-48-8 1-(4-hydroxyphenyl)piperazine 
• 105-39-5 chloroacetic acid ethyl ester 
• 69604-00-8 ethyl 5-nitrobenzo[d]furan-2-carboxylate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 90-02-8 salicylaldehyde 
• 334-22-5 N,N-bis(chloro-2-ethyl)amine 

Downstream Products

• 163521-12-8 vilazodone 

Relevant articles and documents

Design, synthesis, biological evaluation of substituted benzofurans as DNA gyraseB inhibitors of Mycobacterium tuberculosis

DNA gyrase of Mycobacterium tuberculosis (MTB) is a type II topoisomerase and is a well-established and validated target for the development of novel therapeutics. By adapting the medium throughput screening approach, we present the discovery and optimization of ethyl 5-(piperazin-1-yl) benzofuran-2- carboxylate series of mycobacterial DNA gyraseB inhibitors, selected from Birla Institute of Technology and Science (BITS) database chemical library of about 3000 molecules. These compounds were tested for their biological activity; the compound 22 emerged as the most active potent lead with an IC50 of 3.2 ± 0.15 μM against Mycobacterium smegmatis DNA gyraseB enzyme and 0.81 ± 0.24 μM in MTB supercoiling activity. Subsequently, the binding of the most active compound to the DNA gyraseB enzyme and its thermal stability was further characterized using differential scanning fluorimetry method.

Synthetic method for vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate

The invention relates to a synthetic method for a vilazodone intermediate, i.e., ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate. The key vilazodone intermediate ethyl 5-(1-piperazinyl)-2-benzofuran-2-carboxylate as shown in a formula I is prepared with 6-nitrocoumarin as a starting raw material through addition, ring opening, intramolecular ring closure, nitro reduction, piperazine ring preparation, etc. The synthetic method is simple in synthetic route, high in the yield of target products and suitable for industrial scale-up production.

A 5 - (piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester synthesis method

The invention discloses a synthesis method of 5-(piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester. The synthesis method comprises the following steps: (1) under the protection of nitrogen, adding zinc powder and tetrahydrofuran to a reactor, dropwise adding TiCl4, adding 2-hydroxyl-5-(piperazin-1-yl) benzaldehyden and glyoxal, and rectifying to obtain 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic aldehyde; (2) adding a sodium hydroxide solution and a copper sulfate solution to the reactor, and adding the 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic aldehyde while stirring to obtain 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic acid; (3) dissolving the 3-[2-hydroxyl-5-(piperazin-1-yl)] phenyl-2-acrylic acid in absolute ethyl alcohol and adding to the reactor, and adding tetrahydrofuran and anhydrous potassium carbonate to obtain the 5-(piperazin-1-yl) benzofuran-2-carboxylic acid ethyl ester. The synthesis route disclosed by the invention is wide in raw material source, simple to operate and outstanding in advantage.