Hydrogen Peroxide → (R)-4-(1-amino-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 84809Notes

Reaction equation

HRID 84809 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH3:14])[C:11]([NH2:13])=[O:12])=[CH:5][C:4]=1[NH:15][C:16]1[S:20][N:19]=[C:18]([CH3:21])[CH:17]=1)#[N:2].C([O-])([O-])=[O:23].[K+].[K+].OO>CS(C)=O>[NH2:13][C:11](=[O:12])[C@H:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]([NH2:2])=[O:23])=[C:4]([NH:15][C:16]2[S:20][N:19]=[C:18]([CH3:21])[CH:17]=2)[CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67510271(R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide

Product 1

HCID 57334337(R)-4-(1-amino-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamideYield 25.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (R)-2-(4-cyano-3-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (127 mg, 0.421 mmol) in DMSO (2 mL), K2CO3 (200 mg, 1.45 mmol) and H2O2 (50% aq., 1.00 mL) were added. After being stirred at 100 C for 5 min, the mixture was purified by HPLC to give the titled compound (34 mg). MS 320.3 (M+H); UV 205.3, 294.6 nm

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-2971af9ec9c3492fb5067e3c61045d9c
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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