4-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one → 5-Fluoro-4-(1-hydroxy-2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

HRID 1474370Notes

Reaction equation

HRID 1474370 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12](C)[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[F:21][C:22]1[C:23]([CH:32]2[CH2:34][O:33]2)=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=1)[C:27]#[N:28]>>[F:21][C:22]1[C:23]([CH:32]([OH:33])[CH2:34][N:17]2[CH2:16][CH2:15][N:14]([CH2:13][CH2:12][C:3]3[CH:4]=[CH:5][C:6]4[C:7](=[O:11])[O:8][CH2:9][C:10]=4[C:2]=3[CH3:1])[CH2:19][CH2:18]2)=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=1)[C:27]#[N:28]

Participants

3

Reactant 2

HCID 595686964-Methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-oneHCID 866473025-Fluoro-2-methoxy-4-oxiran-2-ylbenzonitrile

Product 1

HCID 498047785-Fluoro-4-(1-hydroxy-2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile

Procedure

5-fluoro-4-(1-hydroxy-2-{4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(methyloxy)benzonitrile was prepared in a similar fashion to that described for the synthesis of EXAMPLE 12 starting from 4-methyl-5-(1-methyl-2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one and 5-fluoro-2-(methyloxy)-4-oxiran-2-ylbenzonitrile.

Sources & evidence

ORD record
ord-49079311ad90461f811605a3e47764a6
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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