Acetic Acid → (R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(3-methylisothiazol-5-ylamino)pyrazine-2-carboxamide

HRID 332769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332769
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:16][C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19])=[N:7][C:8]=1[NH:9][C:10]1[S:14][N:13]=[C:12]([CH3:15])[CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:31]>CCO.CS(C)=O>[NH2:20][C:18](=[O:19])[C@H:17]([NH:16][C:6]1[N:7]=[C:8]([NH:9][C:10]2[S:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[C:3]([C:1]([NH2:2])=[O:31])=[N:4][CH:5]=1)[CH2:21][CH:22]([CH3:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685572(R)-2-(5-cyano-6-(3-methylisothiazol-5-ylamino)pyrazin-2-ylamino)-4-methylpentanamide

Produkt 1

HCID 71571721(R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(3-methylisothiazol-5-ylamino)pyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

The compound (R)-2-(5-cyano-6-(3-methylisothiazol-5-ylamino)pyrazin-2-ylamino)-4-methylpentanamide (17 mg, 0.049 mmol) was dissolved in EtOH (1 mL) and DMSO (0.5 mL), aq. 1N NaOH (0.50 mL) and aq. H2O2 (30%, 0.50 mL) were added. The mixture was stirred at room temperature for 60 min. HOAc (0.1 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (7 mg). MS 364.3 (M+H); UV 210.2, 275.0, 323.7 nm; t 0.458 min.

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d1376a4f0924409290913824a894f6db
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877760B2

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