(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Base Information

• Chemical Name: (5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone
• CAS No.: 141644-91-9
• Molecular Formula: C30H42N2O3
• Molecular Weight: 478.675
• Hs Code.: 2932999099
• European Community (EC) Number: 604-243-9
• UNII: HJS89VA2WC
• ChEMBL ID: CHEMBL4877298
• DSSTox Substance ID: DTXSID00467457
• Nikkaji Number: J3.309.671B
• Wikidata: Q72439105
• Mol file: 141644-91-9.mol

Synonyms:141644-91-9;(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone;(5-amino-2-butyl-1-benzofuran-3-yl)-[4-[3-(dibutylamino)propoxy]phenyl]methanone;HJS89VA2WC;Methanone, (5-amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]-;(5-AMINO-2-BUTYL-3-BENZOFURANYL)[4-[3-(DIBUTYLAMINO)PROPOXY]PHENYL]METHANONE;CHEMBL4877298;Dronedarone metabolite, SR 33580;(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutyl-amino)propoxy)phenyl)methanone;SR-33580;(5-Amino-2-butyl-3-benzofuranyl)(4-(3-(dibutylamino)propoxy)phenyl)methanone;5-Amino-2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran;Methanone, (5-amino-2-butyl-3-benzofuranyl)(4-(3-(dibutylamino)propoxy)phenyl)-;5-amino-2-butyl-3-(4-[3-(dibutylamino)propoxy]benzoyl)benzofuran;(5-Amino-2-butyl-1-benzofuran-3-yl)-(4-(3-(dibutylamino)propoxy)phenyl)methanone;SPIIBUQYWNFELT-UHFFFAOYSA-N;UNII-HJS89VA2WC;SCHEMBL282404;DTXSID00467457;CS-M0184;BDBM50568189;AKOS015901880;CS-13420;FT-0761833;DRONEDARONE HYDROCHLORIDE IMPURITY B [EP IMPUITY];2-(n-butyl)-3-(4-{3-[di(n-butyl)amino]propoxy}benzoyl)-5-aminobenzofuran;5-amino-3-[4-(3-di-n-butylamino-propoxy)benzoyl]-2-n-butyl benzofuran;(5-Amino-2-butyl-1-benzofuran-3-yl){4-[3-(dibutylamino)propoxy]phenyl}methanone;(5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone

Chemical Property of (5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.564
• Boiling Point: 630.151 °C at 760 mmHg
• PKA: 9.44±0.50(Predicted)
• Flash Point: 334.904 °C
• PSA: 68.70000
• Density: 1.066 g/cm³
• LogP: 7.84090
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 16
• Exact Mass: 478.31954321
• Heavy Atom Count: 35
• Complexity: 584

Purity/Quality:

99.9% ^*data from raw suppliers

(5-Amino-2-butyl-3-benzofuranyl)[4-[3-(dibutylamino)propoxy]phenyl]methanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1=C(C2=C(O1)C=CC(=C2)N)C(=O)C3=CC=C(C=C3)OCCCN(CCCC)CCCC
• 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.

Technology Process of (5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

There total 33 articles about (5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone 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: 98.4%

(2-butyl-5-nitrobenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone (141645-23-0) → (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (141644-91-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; for 0.333333h; under 2584.17 Torr;

Reference yield: 95.0%

4-[3-(dibutylamino)propoxy]benzoic acid + 2-(-2-butyl-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)dione (1365546-05-9) → (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (141644-91-9)

Guidance literature:

4-[3-(dibutylamino)propoxy]benzoic acid; With Eaton’s reagent; for 0.25h;

2-(-2-butyl-1-benzofuran-5-yl)-1H-isoindole-1,3(2H)dione; at 35 ℃; for 1h;

Reference yield: 91.57%

5-amino-2-n-butyl-3-[4-(3-di-n-butylamino propoxy)benzoyl]benzofuran bisoxalate (500791-70-8,851014-95-4) → (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (141644-91-9)

Guidance literature:

With sodium hydroxide; In water; toluene; for 0.5h; pH=10 - 12; Product distribution / selectivity;

upstream raw materials:

(2-butyl-5-nitrobenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

dibutyl-(3-chloro-propyl)-amine

4-methoxy-benzoyl chloride

Downstream raw materials:

N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)-benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide

dronedarone

dronedarone hydrochloride

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

Refernces

• 1、 Chen, Hao,Chen, Xiuhui,Sun, Ping,Wu, Dan,Yue, Hu,Pan, Jintao,Li, Xinxuan,Zhang, Cheng,Wu, Xinyi,Hua, Lei,Hu, Wenhui,Yang, Zhongjin. "Discovery of dronedarone and its analogues as NLRP3 inflammasome inhibitors with potent anti-inflammation activity". supporting information. . Retrieved 2021/06/18.
• 2、 Klucznik, Tomasz,Mikulak-Klucznik, Barbara,McCormack, Michael P.,Lima, Heather,Szymku?, Sara,Bhowmick, Manishabrata,Molga, Karol,Zhou, Yubai,Rickershauser, Lindsey,Gajewska, Ewa P.,Toutchkine, Alexei,Dittwald, Piotr,Startek, Micha? P.,Kirkovits, Gregory J.,Roszak, Rafa?,Adamski, Ariel,Sieredzińska, Bianka,Mrksich, Milan,Trice, Sarah L.J.,Grzybowski, Bartosz A.. "Efficient Syntheses of Diverse, Medicinally Relevant Targets Planned by Computer and Executed in the Laboratory". supporting information. p. 522 - 532. Retrieved 2018/03/21.