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

HRID 335527노트

반응식

HRID 335527 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 82844Platinum oxide (PtO)촉매

실험 절차

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.

출처 및 근거

ORD 기록
ord-cf050c06d8c346c597aa139103af73ea
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884033B2

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