Acetic Acid → 4-(1-Amino-4,4,4-trifluoro-1-oxobutan-2-ylamino)-5-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 2201122Notes

Reaction equation

HRID 2201122 reaction equation
[C:1]([C:3]1[C:8]([NH:9][C:10]2[S:14][N:13]=[C:12]([CH3:15])[CH:11]=2)=[CH:7][C:6]([NH:16][CH:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:18]([NH2:20])=[O:19])=[C:5]([F:26])[CH:4]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:33]>CCO.CS(C)=O>[NH2:20][C:18](=[O:19])[CH:17]([NH:16][C:6]1[C:5]([F:26])=[CH:4][C:3]([C:1]([NH2:2])=[O:33])=[C:8]([NH:9][C:10]2[S:14][N:13]=[C:12]([CH3:15])[CH:11]=2)[CH:7]=1)[CH2:21][C:22]([F:23])([F:25])[F:24]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 675082812-(4-Cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-4,4,4-trifluorobutanamide

Product 1

HCID 675160594-(1-Amino-4,4,4-trifluoro-1-oxobutan-2-ylamino)-5-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To a solution of 2-(4-cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-4,4,4-trifluorobutanamide (98 mg, 0.250 mmol) in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1 mL, 1.0 mmol) and aq. H2O2 (50%, 1 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (1 mL) was added. The mixture was purified by HPLC to give the titled compound (28 mg). MS 406.1 (M+H); UV 204.7, 287.8 nm.

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-56a4efeccf1c496bb1e1d8a3876dab81
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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