4-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}tetrahydropyran-4-carboxylic acid → 4-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-tetrahydropyran-4-carboxylic acid-N-hydroxyamide

HRID 1005899Notes

Reaction equation

HRID 1005899 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][C@H:24]([CH:29]([CH3:31])C)[C:25]([NH:27][OH:28])=[O:26])(=[O:22])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.FC1C=CC(C2C=NC(N3CCN(S(CC4(C(O)=O)CC[O:58][CH2:57][CH2:56]4)(=O)=O)CC3)=NC=2)=CC=1>>[OH:28][NH:27][C:25]([C:24]1([CH2:23][S:20]([N:17]2[CH2:16][CH2:15][N:14]([C:11]3[N:12]=[CH:13][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:9][N:10]=3)[CH2:19][CH2:18]2)(=[O:21])=[O:22])[CH2:29][CH2:31][O:58][CH2:57][CH2:56]1)=[O:26]

Participants

3

Reactant 2

HCID 226467234-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}tetrahydropyran-4-carboxylic acidHCID 235197322-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramide

Product 1

HCID 865847714-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-tetrahydropyran-4-carboxylic acid-N-hydroxyamideYield 92%

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 4-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonyl-methyl}tetrahydropyran-4-carboxylic acid (0.29 g), to provide the title compound as a white solid (0.27 g, 92%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-8f828f8960d54d8dbbc4c85625c08c70
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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