Acetic Acid → (R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(3-phenylisothiazol-5-ylamino)pyrazine-2-carboxamide

HRID 332832Notes

Reaction equation

HRID 332832 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:21][C@H:22]([CH2:26][CH3:27])[C:23]([NH2:25])=[O:24])=[N:7][C:8]=1[NH:9][C:10]1[S:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:34]>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[S:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:11]=2)[C:3]([C:1]([NH2:2])=[O:34])=[N:4][CH:5]=1)[CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685621(R)-2-(5-cyano-6-(3-phenylisothiazol-5-ylamino)pyrazin-2-ylamino)butanamide

Product 1

HCID 89572642(R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(3-phenylisothiazol-5-ylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(3-phenylisothiazol-5-ylamino)pyrazin-2-ylamino)butanamide (8 mg, 0.021 mmol) was dissolved in EtOH (1 mL) and DMSO (0.5 mL), aq. 1N NaOH (0.5 mL) and aq. H2O2 (30%, 0.5 mL) were added. The mixture was stirred at room temperature for 20 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 (5 mg). MS found for C18H19N7O2S as (M+H)+ MS 398.2. UV: λ=UV 201.1, 267.7, 321.9 nm.

Workup

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

Sources & evidence

ORD record
ord-13a1efe371d94ae6be36231f5658db76
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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