6-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one → 5-[(1R)-1-hydroxy-2-{4-[2-hydroxy-2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 1474415Notes

Reaction equation

HRID 1474415 reaction equation
[OH:1][C@H:2]([C:10]1[CH:19]=[CH:18][C:13]2[C:14](=[O:17])[O:15][CH2:16][C:12]=2[C:11]=1[CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:21][C:22]1[C:23]([CH:32]2[CH2:34][O:33]2)=[CH:24][C:25]2[CH2:29][O:28][C:27](=[O:30])[C:26]=2[CH:31]=1>>[OH:1][C@H:2]([C:10]1[CH:19]=[CH:18][C:13]2[C:14](=[O:17])[O:15][CH2:16][C:12]=2[C:11]=1[CH3:20])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:34][CH:32]([OH:33])[C:23]2[C:22]([CH3:21])=[CH:31][C:26]3[C:27](=[O:30])[O:28][CH2:29][C:25]=3[CH:24]=2)[CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 595686626-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-oneHCID 595687285-[(1R)-1-hydroxy-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 595686595-[(1R)-1-hydroxy-2-{4-[2-hydroxy-2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl]-4-methyl-2-benzofuran-1(3H)-one

Procedure

5-[(1R)-1-hydroxy-2-{4-[2-hydroxy-2-(6-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl]-4-methyl-2-benzofuran-1(3H)-one was prepared in a similar fashion to that described for the synthesis of EXAMPLE 58 starting from 5-[(1R)-1-hydroxy-2-(piperazin-1-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one and isomer B of 6-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (65B).

Sources & evidence

ORD record
ord-9e3243663acd48f48a69dbcfaabef270
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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