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

HRID 2200442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200442
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:21][C@H:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([NH2:25])=[O:24])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:36]>CCO.CS(C)=O>[NH2:25][C:23](=[O:24])[C@H:22]([NH:21][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:20][N:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[C:3]([C:1]([NH2:2])=[O:36])=[N:4][CH:5]=1)[CH2:26][CH:27]([CH3:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685570(R)-2-(5-cyano-6-(4-(isoxazol-5-yl)phenylamino)pyrazin-2-ylamino)-4-methylpentanamide

Produkt 1

HCID 86685571(R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

The compound (R)-2-(5-cyano-6-(4-(isoxazol-5-yl)phenylamino)pyrazin-2-ylamino)-4-methylpentanamide (5 mg, 0.012 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 30 min. HOAc (0.2 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (3 mg). MS 410.3 (M+H); UV 202.3, 235.2, 276.9, 331.2 nm; t 0.627 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0c4f2b0b8f12409f894ddfb26b1e94be
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359308B2

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