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

HRID 2200440Notes

Reaction equation

HRID 2200440 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:18][C@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH2:22])=[O:21])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)#[N:2].[OH-:27].[Na+].[OH:29]O.CC(O)=O>CCO.CS(C)=O>[NH2:22][C:20](=[O:21])[C@H:19]([NH:18][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:16](=[O:29])[NH2:17])=[CH:14][CH:15]=2)[C:3]([C:1]([NH2:2])=[O:27])=[N:4][CH:5]=1)[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685568(R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)-4-methylpentanamide

Product 1

HCID 86685569(R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(4-carbamoylphenylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(4-cyanophenylamino)pyrazin-2-ylamino)-4-methylpentanamide (57 mg, 0.163 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 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 (46 mg). MS 386.4 (M+H); UV 206.0, 269.5, 325.6 nm; t 0.475 min.

Workup

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

Sources & evidence

ORD record
ord-09faaa4bafb14202ab77f7536c81887b
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

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