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

HRID 332767Notes

Reaction equation

HRID 332767 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:21][C@H:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([NH2:25])=[O:24])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:36]>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[CH:15]=[CH:14][C:13]([C:16]3[O:20][N:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[C:3]([C:1]([NH2:2])=[O:36])=[N:4][CH:5]=1)[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685570(R)-2-(5-cyano-6-(4-(isoxazol-5-yl)phenylamino)pyrazin-2-ylamino)-4-methylpentanamide

Product 1

HCID 86685571(R)-5-(1-amino-4-methyl-1-oxopentan-2-ylamino)-3-(4-(isoxazol-5-yl)phenylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(4-(isoxazol-5-yl)phenylamino)pyrazin-2-ylamino)-4-methylpentanamide (5 mg, 0.012 mmol) was dissolved in EtOH (1 mL) and DMSO (0.5 mL), aq. 1N NaOH (0.50 mL) and aq. H2O2 (30%, 0.50 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (0.2 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (3 mg). MS 410.3 (M+H); UV 202.3, 235.2, 276.9, 331.2 nm; t 0.627 min.

Workup

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

Sources & evidence

ORD record
ord-14527cb841454a05a087a141acb16064
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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