2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramide → 2-(R)-{4-[5-(4-Chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methylbutyramide

HRID 393749Notes

Reaction equation

HRID 393749 reaction equation
FC1C=CC(C2C=NC(N3CCN(S(C[C@H](C(C)C)C([NH:27][OH:28])=O)(=O)=O)CC3)=NC=2)=CC=1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[CH:41][C:42]([N:45]3[CH2:50][CH2:49][N:48]([S:51]([CH2:54][C@H:55]([CH:59]([CH3:61])[CH3:60])[C:56](O)=[O:57])(=[O:53])=[O:52])[CH2:47][CH2:46]3)=[N:43][CH:44]=2)=[CH:35][CH:34]=1>>[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:40]=[CH:41][C:42]([N:45]3[CH2:46][CH2:47][N:48]([S:51]([CH2:54][C@H:55]([CH:59]([CH3:61])[CH3:60])[C:56]([NH:27][OH:28])=[O:57])(=[O:53])=[O:52])[CH2:49][CH2:50]3)=[N:43][CH:44]=2)=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 235197322-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramideHCID 235197362-(R)-{4-[5-(4-Chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid

Product 1

HCID 235197282-(R)-{4-[5-(4-Chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methylbutyramideYield 76%

Procedure

Prepared according to the method for the preparation of 2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramide, from 2-(R)-{4-[5-(4-chlorophenyl)pyridin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid (0.068 g), to provide the title compound as a cream solid (0.053 g, 76%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c2c2efa27f2246a4bb16deb1548fde27
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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