2-Methoxy-4-(oxiran-2-yl)benzonitrile → 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 1187119Notes

Reaction equation

HRID 1187119 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.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([CH:31]2[CH2:33][O:32]2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>>[OH:32][CH:31]([C:29]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([O:22][CH3:21])[CH:30]=1)[CH2:33][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[C:10]2[CH:19]=[CH:18][C:13]3[C:14](=[O:17])[O:15][CH2:16][C:12]=3[C:11]=2[CH3:20])[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 552967592-Methoxy-4-(oxiran-2-yl)benzonitrileHCID 595687245-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 498007534-(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

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 2-(methyloxy)-4-oxiran-2-ylbenzonitrile.

Sources & evidence

ORD record
ord-4b0b7a45b4c845f9958fb61a622c5b2e
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…