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

HRID 1187121Notes

Reaction equation

HRID 1187121 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][C:22]1[C:23]([O:33][CH3:34])=[C:24]([CH:27]=[CH:28][C:29]=1[CH:30]1[CH2:32][O:31]1)[C:25]#[N:26]>>[OH:31][CH:30]([C:29]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([O:33][CH3:34])[C:22]=1[CH3:21])[CH2:32][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 595687245-(1-hydroxy-2-piperazin-1-ylethyl)-4-methyl-2-benzofuran-1(3H)-oneHCID 772312543-Methyl-2-(methyloxy)-4-oxiran-2-ylbenzonitrile

Product 1

HCID 498007554-(1-Hydroxy-2-{4-[2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-3-methyl-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)-3-methyl-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 3-methyl-2-(methyloxy)-4-oxiran-2-ylbenzonitrile.

Sources & evidence

ORD record
ord-854a885dd91146f495db51d01a169de6
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…