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

HRID 393753Notes

Reaction equation

HRID 393753 reaction equation
F[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])[CH3:30])[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.[C:32](C1C=CC(C2C=NC(N3CCN(S(C[C@H](C(C)C)C(O)=O)(=O)=O)CC3)=NC=2)=CC=1)#[N:33]>>[C:32]([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]([CH3:30])[CH3:31])[C:25]([NH:27][OH:28])=[O:26])(=[O:21])=[O:22])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1)#[N:33]

Participants

3

Reactant 2

HCID 235197322-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methyl-butyramideHCID 235197382-(R)-{4-[5-(4-Cyanophenyl)-pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric Acid

Product 1

HCID 235197392-(R)-{4-[5-(4-Cyanophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-N-hydroxy-3-methylbutyramideYield 53%

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-Cyanophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid (0.070 g), to provide the title compound as a white solid (0.039 g, 53%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-255c94c630ed497cbb7280a09439093a
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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