141644-91-9

Basic information

• Product Name: (5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone
• Synonyms: (5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone;(5-Amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone;Methanone, (5-amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]-;Dronedarone impurity A
• CAS NO: 141644-91-9
• Molecular Formula: C₃₀H₄₂N₂O₃
• Molecular Weight: 478.67
• EINECS: 1806241-263-5
• Mol File: 141644-91-9.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 630.151 °C at 760 mmHg
• Flash Point: 334.904 °C
• Appearance: /
• Density: 1.066
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.44±0.50(Predicted)
• CAS DataBase Reference: (5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(141644-91-9)
• EPA Substance Registry System: (5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone(141644-91-9)

Safety Data

• Hazardous Substances Data: 141644-91-9(Hazardous Substances Data)

Usage

Uses

(5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone is an intermediate used in the synthesis of dronedarone hydrochloride (I), a class III antiarrhythmia drug for the prevention of cardiac arrhythmias such as atrial fibrillation.

InChI:InChI=1/C30H42N2O3/c1-4-7-11-28-29(26-22-24(31)14-17-27(26)35-28)30(33)23-12-15-25(16-13-23)34-21-10-20-32(18-8-5-2)19-9-6-3/h12-17,22H,4-11,18-21,31H2,1-3H3

Upstream product

• 141645-16-1 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran 
• 36421-15-5 dibutyl-(3-chloro-propyl)-amine 
• 114980-27-7 4-<3-(dibutylamino)propoxy>benzaldehyde 
• 1278585-69-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)acetamide 
• 478158-85-9 4-(3-di-n-butylaminopropoxy)benzoyl chloride 
• 526196-92-9 (2-n-butyl-benzofuran-5-yl)-acetamide 
• 1365546-05-9 2-(-2-butyl-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)dione 
• 111-92-2 dibutylamine 
• 65136-52-9 4-(3-chloropropoxy)benzoic acid 
• 65136-48-3 4-(3-chloropropoxy)benzoic acid chloride 
• 526196-90-7 2-n-butyl-5-aminobenzofuran hydrochloride 
• 1365546-06-0 3-[4-(3-chloropropoxy)benzoyl]-2-n-butylbenzofuran-5-yl-1H-isoindole-1,3(2H)dione 
• 1365546-07-1 C₃₈H₄₄N₂O₅ 
• 500791-70-8 5-amino-2-n-butyl-3-[4-(3-di-n-butylamino propoxy)benzoyl]benzofuran bisoxalate 

Downstream Products

• 141626-57-5 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide 
• 141626-36-0 dronedarone 
• 141625-93-6 dronedarone hydrochloride 
• 141625-93-6 2-(n-butyl)-3-(4-{3-[di(n-butyl)amino]propoxy}benzoyl)-5-(methanesulfonamido)benzofuran hydrochloride 

Relevant articles and documents

Concise total synthesis of antiarrhythmic drug dronedarone via a conjugate addition followed intramolecular heck cyclization

A concise, scalable, and an efficient total synthesis for dronedarone (2) was described using conjugate addition followed by intramolecular Heck cyclization. The other key reaction includes selective reduction of nitro functionality and addition of lithiated terminal alkyne to the aldehyde. The overall yield of this approach is 44% in six steps.

Benzofuran compound and application thereof

The invention provides a benzofuran compound as shown in a formula (I) or pharmaceutically acceptable salt thereof, and application thereof. The compound can selectively inhibit activation of NLRP3 inflammasomes and inhibit maturation and secretion of inflammation activation signal molecules Caspase-1 and P20 and inflammatory cytokines IL-1beta, has a good prevention and treatment effect on NLRP3 inflammasome related diseases, and particularly has a remarkable prevention and treatment effect on peritonitis and gouty arthritis. Therefore, the compound can be used for preparing drugs for treating NLRP3 inflammasome-related diseases, such as anti-inflammatory drugs or auxiliary anti-inflammatory drugs.

2-butyl-3 - (4-substituted propoxy benzoyl) - 5-substituted aminobenzofuran preparation method

The invention discloses a method for preparing 2-n-butyl-3-(4-substituted-propoxybenzoyl)-5-substituted aminobenzofuran, which comprises the steps of: dissolving a compound shown as a formula (III) into a solvent, adding a compound shown as a formula (V) into the obtained solution, reacting under the catalysis of a Lewis acid, and then collecting the 2-n-butyl-3-(4-substituted-propoxybenzoyl)-5-substituted aminobenzofuran (IV) from a reaction product. The method not only ensures that chemical structures of adopted raw materials and intermediates are all different, but also avoids using expensive metal catalysts and reaction conditions of high-pressure hydrogenation, greatly reduces the preparation cost for 2-n-butyl-3-(4-(3-di-n-butylaminopropoxy)benzoyl)-5-aminobenzofuran, is more suitable for industrialized mass preparation, and is higher in positive progress effect and actual application value, and apparent in competitive advantages compared with a reported literature method. A reaction formula is as follows.