Acetic Acid → (R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide

HRID 2200395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200395
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:20][C@H:21]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:22]([NH2:24])=[O:23])=[N:7][C:8]=1[NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[CH:13]2)#[N:2].[OH-].[Na+].OO.CC(O)=[O:35]>CCO.CS(C)=O>[NH2:24][C:22](=[O:23])[C@H:21]([NH:20][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:3]([C:1]([NH2:2])=[O:35])=[N:4][CH:5]=1)[CH2:25][CH:26]([CH3:28])[CH3:27]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685530(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-4-methylpentanamide

Produkt 1

HCID 86685531(R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

The crude (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-4-methylpentanamide (151 mg) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (50%, 1.0 mL) were added. The mixture was stirred at room temperature for 60 min. HOAc (0.5 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (21 mg). MS 394.2 (M+H); UV 201.1, 265.8, 297.2, 358.5 nm; t 0.451 min.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d37c38192fce419e8552df075dcc5732
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359308B2

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