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

HRID 1474411Notes

Reaction equation

HRID 1474411 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.[Cl:21][C:22]1[CH:23]=[C:24]([C:31]#[N:32])[CH:25]=[N:26][C:27]=1[CH:28]1[CH2:30][O:29]1>>[Cl:21][C:22]1[CH:23]=[C:24]([C:31]#[N:32])[CH:25]=[N:26][C:27]=1[CH:28]([OH:29])[CH2:30][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 595687195-Chloro-6-(oxiran-2-yl)pyridine-3-carbonitrileHCID 595687285-[(1R)-1-hydroxy-2-piperazin-1-ylethyl]-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 498022225-Chloro-6-[1-hydroxy-2-[4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-3H-isobenzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]pyridine-3-carbonitrile

Procedure

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

Sources & evidence

ORD record
ord-319de6a6d6084d798d08b119293361c1
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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