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

HRID 335527Notes

Reaction equation

HRID 335527 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[O:13][C:12]2[CH:11]=[CH:10][C:9]([NH:14]S(C)(=O)=O)=[CH:8][C:7]=2[C:6]=1[C:19]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30][N:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:25][CH:26]=1)=[O:20].C(C1OC2C=CC([N+]([O-])=O)=CC=2C=1C(=O)C1C=CC(OCCCN(CCCC)CCCC)=CC=1)CCC.[H][H]>[Pt]=O>[CH2:4]([C:5]1[O:13][C:12]2[CH:11]=[CH:10][C:9]([NH2:14])=[CH:8][C:7]=2[C:6]=1[C:19](=[O:20])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][N:31]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:22]=1)[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 208898DronedaroneHCID 10209258(2-Butyl-5-nitrobenzofuran-3-yl)(4-(3-dibutylaminopropoxy)phenyl)methanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 11488441(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A process for the preparation of dronedarone was reported in the above said patent EP 0 471 609, according to which process 2-(n-butyl)-3-(4-{3-[di(n-butyl)amino]propoxy}benzoyl)-5-nitrobenzofuran is reduced under pressure with hydrogen in the presence of platinum oxide as catalyst to form 2-(n-butyl)-3-(4-{3-[di(n-butyl)amino]propoxy}benzoyl)-5-aminobenzofuran (hereinafter Compound A), which is subsequently treated with methanesulfonyl chloride, in the presence of an acid acceptor, to give the desired compound. According to this process, dronedarone could be obtained with an overall yield of the order of 60%, starting from the 5-nitrobenzofuran derivative.

Sources & evidence

ORD record
ord-cf050c06d8c346c597aa139103af73ea
Source dataset
uspto-grants-2014_11
Patent number
US08884033B2

Reaction notes

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