DRONEDARONE HYDROCHLORIDE

Base Information

• Chemical Name: DRONEDARONE HYDROCHLORIDE
• CAS No.: 141625-93-6
• Molecular Formula: C₃₁H₄₄N₂O₅S*ClH
• Molecular Weight: 593.228
• Hs Code.: 2935904000
• Mol file: 141625-93-6.mol

Synonyms:Methanesulfonamide,N-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]-,monohydrochloride (9CI);Dronedarone HCl;SR 33589B;SR33598B;UNII-FA36DV299Q;

Chemical Property of DRONEDARONE HYDROCHLORIDE

Chemical Property:

• Vapor Pressure: 1.47E-18mmHg at 25°C
• Melting Point: NA (low-melting)
• Boiling Point: 683.9 °C at 760 mmHg
• Flash Point: 367.4 °C
• PSA: 97.23000
• LogP: 9.00480
• Storage Temp.: Refrigerator
• Solubility.: DMSO: soluble15mg/mL, clear

Purity/Quality:

99%min ^*data from raw suppliers

Dronedarone Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dronedarone Hydrochloride is a therapy for the treatment of patients with paroxysmal and persistent atrial fibrillation or atrial flutter. Cardiovascular Drugs Dronedarone Hydrochloride can be used for the treatment of atrial fibrillation and atrial flutter in patients who have suffered cardiac arrhythmias.
• Clinical Use: Dronedarone hydrochloride (also known as SR33589 and marketed as Multaq) is a drug developed by Sanofi-Aventis for cardiac arrhythmias (irregular heartbeat) that was approved by the FDA in July 2009. Dronedarone is used for the treatment of atrial fibrillation and atrial flutter in patients whose hearts have either returned to normal rhythm or who undergo drug therapy or electroshock treatment to maintain normal cardio rhythm. Dronedarone is less lipophilic than amiodarone, exhibits a much smaller volume of distribution and a half-life of 24 h, this stands in contrast to competitor amiodarone’s half-life of several weeks. As a result of these pharmacokinetic characteristics, dronedarone dosing may be less complicated than amiodarone.

Technology Process of DRONEDARONE HYDROCHLORIDE

There total 21 articles about DRONEDARONE HYDROCHLORIDE 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: 98.0%

dronedarone (141626-36-0) → dronedarone hydrochloride (141625-93-6)

Guidance literature:

With hydrogenchloride; In diethyl ether; ethyl acetate; at 0 - 20 ℃; for 2.08333h;

DOI:10.1016/j.bmc.2018.03.041

Reference yield: 96.0%

(5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (141644-91-9) + methanesulfonyl chloride (124-63-0) → 2-(n-butyl)-3-(4-{3-[di(n-butyl)amino]propoxy}benzoyl)-5-(methanesulfonamido)benzofuran hydrochloride (141625-93-6)

Guidance literature:

(5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone; methanesulfonyl chloride; With ammonium hydroxide; In tetrahydrofuran; tert-butyl methyl ether; at 25 - 30 ℃; Large scale;

With hydrogenchloride; In water; isopropyl alcohol; at 50 - 55 ℃; Large scale;

Reference yield: 94.0%

(5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (141644-91-9) + methanesulfonyl chloride (124-63-0) → dronedarone hydrochloride (141625-93-6)

Guidance literature:

tetramethlyammonium chloride; In toluene; Product distribution / selectivity; Reflux;

upstream raw materials:

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide

dronedarone

3-{4-[(2-butyl-5-methanesulfonamide-1-benzofuran-3-yl)carbonyl]phenoxy}propyl methanesulfonate

dibutylamine

Downstream raw materials:

N-[2-butyl-3-[4-(3-(di-n-butylamino)propoxy)benzoyl]-5-benzofuranyl]methanesulfonamide hydrobromide

Refernces

• 1、 Mali, Anil C.,Ippar, Sharad S.,Bodke, Mahendra B.,Patil, Nilesh S.,Mathad, Vijayavitthal T.. "An improved and efficient process for the production of dronedarone hydrochloride, an antiarrhythmia drug". . p. 863 - 868. Retrieved 2013.
• 2、 Piotrkowska, Barbara,Nerdinger, Sven,Schreiner, Erwin,Seli?, Lovro,Graczyk, Piotr P.. "A short synthesis of Dronedarone". . p. 4330 - 4335. Retrieved 2018/05/04.
• 3、 -. "PROCESS FOR PREPARING DRONEDARONE AND SALTS THEREOF". Page/Page column 13; 14; 15. . Retrieved 2015/03/16.