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

HRID 2200457Notes

Reaction equation

HRID 2200457 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([NH:19][C@H:20]([CH2:24][CH3:25])[C:21]([NH2:23])=[O:22])[CH:16]=[N:15][C:14]=2[C:26]#[N:27])=[CH:8][CH:7]=1.[OH-].[Na+].OO.CC(O)=[O:34]>CCO.CS(C)=O>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:14]([C:26]([NH2:27])=[O:34])=[N:15][CH:16]=[C:17]([NH:19][C@H:20]([CH2:24][CH3:25])[C:21]([NH2:23])=[O:22])[N:18]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685582(R)-2-(6-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)butanamide

Product 1

HCID 71571722(R)-3-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-(1-amino-1-oxobutan-2-ylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(6-(4-(1,3,4-oxadiazol-2-yl)phenylamino)-5-cyanopyrazin-2-ylamino)butanamide (57 mg, 0.156 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 (0.5 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (3 mg). MS 383.3 (M+H); UV 204.7, 275.5, 329.8 nm; t 0.449 min.

Workup

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

Sources & evidence

ORD record
ord-19d52bda65e048dfb1519b1b896599e2
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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