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

HRID 2200501Notes

Reaction equation

HRID 2200501 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:16][C@H:17]([CH2:21][CH3:22])[C:18]([NH2:20])=[O:19])=[N:7][C:8]=1[NH:9][C:10]1[S:14][N:13]=[C:12]([CH3:15])[CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:29]>CCO.CS(C)=O>[NH2:20][C:18](=[O:19])[C@H:17]([NH:16][C:6]1[N:7]=[C:8]([NH:9][C:10]2[S:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[C:3]([C:1]([NH2:2])=[O:29])=[N:4][CH:5]=1)[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685617(R)-2-(5-cyano-6-(3-methylisothiazol-5-ylamino)pyrazin-2-ylamino)butanamide

Product 1

HCID 86685618(R)-5-(1-amino-1-oxobutan-2-ylamino)-3-(3-methylisothiazol-5-ylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(3-methylisothiazol-5-ylamino)pyrazin-2-ylamino)butanamide (106 mg, 0.334 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 15 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 (38 mg). MS found for C13H17N7O2S as (M+H)+ MS 336.2; UV 206.0, 275.0, 323.1 nm; t 0.365 min. 1H NMR: (CD3OD) δ 7.70 (s, 1H), 6.88 (s, 1H), 4.65 (br.s, 1H), 2.45 (s, 3H), 2.18-2.05 (m, 1H), 1.96-1.87 (m, 1H), 1.10 (t, 3H).

Workup

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

Sources & evidence

ORD record
ord-7d897d3acbae43bc9df0f2684ee12804
Source dataset
uspto-grants-2016_06
Patent number
US09359308B2

Reaction notes

Loading…