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

HRID 1187120Notes

Reaction equation

HRID 1187120 reaction equation
[OH:1][CH: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.[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:7]2[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[C:10]3[CH:19]=[CH:18][C:13]4[C:14](=[O:17])[O:15][CH2:16][C:12]=4[C:11]=3[CH3:20])[CH2:5][CH2:6]2)=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:29]=1)[C:27]#[N:28]

Participants

3

Reactant 2

HCID 595687245-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-oneHCID 866473025-Fluoro-2-methoxy-4-oxiran-2-ylbenzonitrile

Product 1

HCID 498007545-Fluoro-4-(1-hydroxy-2-{4-[2-hydroxy-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-hydroxy-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 EXAMPLES 2C and 28-29 starting from 5-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one and 5-fluoro-2-(methyloxy)-4-oxiran-2-ylbenzonitrile. LC/MS (M+1)+=470.56.

Sources & evidence

ORD record
ord-438e91e0636a4ef2acf0b38b185566f3
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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