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Acetic Acid → (R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(4-(pyridin-3-yl)phenylamino)pyrazine-2-carboxamide

HRID 2200463
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2200463
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:22][C@H:23]([CH2:27][CH3:28])[C:24]([NH2:26])=[O:25])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:35]>CCO.CS(C)=O>[NH2:26][C:24](=[O:25])[C@H:23]([NH:22][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][CH:15]=2)[C:3]([C:1]([NH2:2])=[O:35])=[N:4][CH:5]=1)[CH2:27][CH3:28]
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Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685585(R)-2-(5-cyano-6-(4-(pyridin-3-yl)phenylamino)pyrazin-2-ylamino)butanamide

Produkt 1

HCID 71571723(R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(4-(pyridin-3-yl)phenylamino)pyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 702EthanolLösungsmittel

Versuchsvorschrift

The compound (R)-2-(5-cyano-6-(4-(pyridin-3-yl)phenylamino)pyrazin-2-ylamino)butanamide (90 mg, 0.241 mmol) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (30%, 1.0 mL) were added. The mixture was stirred at room temperature for 20 min. HOAc (0.1 mL) was added. The mixture was then concentrated in vacuo. To the residue, CH3CN (6 mL) and H2O (8 mL) were added to induce precipitation. The precipitate was collected by filtration, and dried on vacuum to give the titled compound (40 mg). The filtrate was purified by HPLC to give additional titled compound (11 mg). MS 392.3 (M+H); UV 202.3, 235.8, 274.4, 336.1 nm; t 0.404 min.

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionTo the residue, CH3CN (6 mL) and H2O (8 mL) were added
  3. customprecipitation
  4. filtrationThe precipitate was collected by filtration
  5. customdried on vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b87f6115d5be4a8da54b7c25675b1722
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359308B2

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