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

HRID 393756Notes

Reaction equation

HRID 393756 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]=[N:41][C:42]([CH: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:38]=[CH:37][C:36]([C:39]2[CH:40]=[N:41][C:42]([CH:45]3[CH2:50][CH2:49][N:48]([S:51]([CH2:54][C@H:55]([CH:59]([CH3:61])[CH3:60])[C:56]([NH:27][OH:28])=[O:57])(=[O:52])=[O:53])[CH2:47][CH2:46]3)=[N:43][CH:44]=2)=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 235197322-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramideHCID 235197372-(R)-{4-[5-(4-Chlorophenyl)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-3-methylbutyric acid

Product 1

HCID 235197292-(R)-{4-[5-(4-Chlorophenyl)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-N-hydroxy-3-methylbutyramideYield 82%

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-methylbutyramide, from 2-(R)-{4-[5-(4-chlorophenyl)pyrimidin-2-yl]piperidine-1-sulfonylmethyl}-3-methylbutyric acid (0.172 g), to give the title compound as a cream solid (0.146 g, 82%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f0b85a81b11540639aced79447c9f0f0
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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