Dronedarone → 2-Butylbenzofuran-5-amine

HRID 522536Notes

Reaction equation

HRID 522536 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]=1C(C1C=CC(OCCCN(CCCC)CCCC)=CC=1)=O.C(C1OC2C=CC([N+]([O-])=O)=CC=2C=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[CH:6]=1)[CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 208898DronedaroneHCID 98373582-Butyl-5-nitrobenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 98133112-Butylbenzofuran-5-amine

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A process for synthesizing dronedarone was described in patent application WO 02/48132, mentioned previously, using 2-n-butyl-5-nitrobenzofuran, which is reduced, under pressure with hydrogen in the presence of platinum oxide as catalyst to form 2-n-butyl-5-aminobenzofuran. This benzofuran derivative is then subjected to the action of methanesulfonyl chloride, which gives 2-n-butyl-5-methanesulfonamidobenzofuran, which is treated with 4-[3-(di-n-butylamino)propoxy]benzoyl chloride to obtain dronedarone.

Sources & evidence

ORD record
ord-2f212b1e98fe444a8d6dbe3c7b91b1ad
Source dataset
uspto-grants-2016_05
Patent number
US09334254B2

Reaction notes

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