2-Methyl-6-(oxiran-2-yl)nicotinonitrile → 6-[1-Hydroxy-2-[4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-3H-isobenzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-2-methyl-pyridine-3-carbonitrile

HRID 1474410Notes

Reaction equation

HRID 1474410 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:27]([C:28]#[N:29])=[CH:26][CH:25]=[C:24]([CH:30]2[CH2:32][O:31]2)[N:23]=1>>[OH:31][CH:30]([C:24]1[N:23]=[C:22]([CH3:21])[C:27]([C:28]#[N:29])=[CH:26][CH:25]=1)[CH2:32][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][C@H:2]([OH:1])[C:10]2[C:11]([CH3:20])=[C:12]3[C:13](=[CH:18][CH:19]=2)[C:14](=[O:17])[O:15][CH2:16]3)[CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 595687072-Methyl-6-(oxiran-2-yl)nicotinonitrileHCID 595687285-[(1R)-1-hydroxy-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 595686506-[1-Hydroxy-2-[4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-3H-isobenzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-2-methyl-pyridine-3-carbonitrile

Procedure

6-[1-Hydroxy-2-[4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-3H-isobenzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-2-methyl-pyridine-3-carbonitrile 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 2-methyl-6-(oxiran-2-yl)pyridine-3-carbonitrile.

Sources & evidence

ORD record
ord-09e9595a80744c14b700f38d76f9fcf4
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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