2-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acid → 2-(R)-{4-[5-(4-Cyanophenyl)-pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric Acid

HRID 1005876Notes

Reaction equation

HRID 1005876 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:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])(=[O:22])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C([C@@H:38]1COC(=O)[N:39]1C([C@@H](C(C)C)CS(N1CCN(C2N=CC(C3C=CC(C#N)=CC=3)=CN=2)CC1)(=O)=O)=O)C1C=CC=CC=1>>[C:38]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][C:11]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][C@H:24]([CH:28]([CH3:29])[CH3:30])[C:25]([OH:27])=[O:26])(=[O:21])=[O:22])[CH2:16][CH2:15]3)=[N:10][CH:9]=2)=[CH:4][CH:3]=1)#[N:39]

Participants

3

Reactant 2

HCID 235197432-(R)-{4-[5-(4-Fluorophenyl)pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric acidHCID 235197474-(2-{4-[2-(R)-(4-(R)-Benzyl-2-oxooxazolidine-3-carbonyl)-3-methylbutane-1-sulfonyl]piperazin-1-yl}pyrimidin-5-yl)benzonitrile

Product 1

HCID 235197382-(R)-{4-[5-(4-Cyanophenyl)-pyrimidin-2-yl]piperazine-1-sulfonylmethyl}-3-methylbutyric AcidYield 14%

Procedure

Prepared according to the method for the preparation of 2-(R)-{4-[5-(4 fluorophenyl)pyrimidin-2-yl] piperazine-1-sulfonylmethyl}-3-methylbutyric acid, from 4-(2-{4-[2-(R)-(4-(R)-benzyl-2-oxooxazolidine-3-carbonyl)-3-methylbutane-1-sulfonyl]piperazin-1-yl}pyrimidin-5-yl)benzonitrile (0.70 g), to give the title compound as a white solid (0.07 g, 14%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5772b8b71e834b6e997a7fa1243268e1
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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