Hydrogen Peroxide → (R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-2-(3-methylisoxazol-5-ylamino)benzamide

HRID 2201044

Reaction equation

HRID 2201044 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([NH2:13])=[O:12])=[CH:5][C:4]=1[NH:18][C:19]1[O:23][N:22]=[C:21]([CH3:24])[CH:20]=1)#[N:2].C([O-])([O-])=[O:26].[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:26])=[C:4]([NH:18][C:19]2[O:23][N:22]=[C:21]([CH3:24])[CH:20]=2)[CH:5]=1)[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67508850(R)-2-(4-cyano-3-(3-methylisoxazol-5-ylamino)phenylamino)-4-methylpentanamide

Product 1

HCID 67775934(R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-2-(3-methylisoxazol-5-ylamino)benzamideYield 4.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (R)-2-(4-cyano-3-(3-methylisoxazol-5-ylamino)phenylamino)-4-methylpentanamide (20 mg, 0.061 mmol) in DMSO (1 mL), K2CO3 (150 mg, 1.08 mmol) and H2O2 (50% aq., 0.800 mL) were added. After being stirred at 90 C for 5 min, the mixture was purified by HPLC to give the titled compound (1 mg). MS 346.3 (M+H); UV 202.2, 279.2 nm

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-991c890350344bd6a322a8392ca02051
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Linked notes

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