1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid → 1-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid-N-hydroxy-amide

HRID 1005907Notes

Reaction equation

HRID 1005907 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.F[C:33]1[CH:38]=CC(C2C=NC(N3CCN(S(CC4(C(O)=O)CCCCC4)(=O)=O)CC3)=NC=2)=C[CH:34]=1>>[OH:28][NH:27][C:25]([C:24]1([CH2:23][S:20]([N:17]2[CH2:18][CH2:19][N:14]([C:11]3[N:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:13][N:12]=3)[CH2:15][CH2:16]2)(=[O:21])=[O:22])[CH2:38][CH2:33][CH2:34][CH2:31][CH2:29]1)=[O:26]

Participants

3

Reactant 2

HCID 226467411-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acidHCID 235197322-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramide

Product 1

HCID 102275071-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid-N-hydroxy-amideYield 18%

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 1-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}cyclohexanecarboxylic acid (0.241 g), to yield the title compound as a white solid (0.045 g, 18%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6049a7d826064484893bef0e8c9b57ef
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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