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

HRID 332784Notes

Reaction equation

HRID 332784 reaction equation
[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:21]=[CH:20][N:19]=[CH:18][CH:17]=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:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)[C:3]([C:1]([NH2:2])=[O:35])=[N:4][CH:5]=1)[CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685583(R)-2-(5-cyano-6-(4-(pyridin-4-yl)phenylamino)pyrazin-2-ylamino)butanamide

Product 1

HCID 86685584(R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(4-(pyridin-4-yl)phenylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(4-(pyridin-4-yl)phenylamino)pyrazin-2-ylamino)butanamide (57 mg, 0.152 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 30 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 (31 mg). MS 392.3 (M+H); UV 204.2, 244.4, 281.2, 360.0 nm; t 0.404 min.

Workup

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

Sources & evidence

ORD record
ord-a71a98700c5946acacc8329adb9751b2
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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