Ethanol → (R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-2-fluoro-6-(3-methylisothiazol-5-ylamino)benzamide

HRID 2201063Notes

Reaction equation

HRID 2201063 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][C@H:17]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:18]([NH2:20])=[O:19])=[CH:5][C:4]=1[F:25])#[N:2].CC[OH:28]>CS(C)=O.[OH-].[Na+].OO>[NH2:20][C:18](=[O:19])[C@H:17]([NH:16][C:6]1[CH: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:28])=[C:4]([F:25])[CH:5]=1)[CH2:21][CH:22]([CH3:23])[CH3:24]

Participants

6

Reactant 2

HCID 702EthanolHCID 67510110(R)-2-(4-cyano-3-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-4-methylpentanamide

Product 1

HCID 67508664(R)-4-(1-amino-4-methyl-1-oxopentan-2-ylamino)-2-fluoro-6-(3-methylisothiazol-5-ylamino)benzamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 784Hydrogen PeroxideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (R)-2-(4-cyano-3-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-4-methylpentanamide (38 mg, 0.105 mmol) in EtOH (1 mL) and DMSO (0.5 mL), 1N aq. NaOH (0.4 mL) and H2O2 (50% aq., 0.4 mL) were added. After being stirred at room temperature for 1 h, the mixture was concentrated in vacuo. The residue was acidified with HOAc (0.5 mL), and then was purified by HPLC to give the titled compound (18 mg). MS 380.3 (M+H); UV 221.1, 282.9, 297.7 nm

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-338db526521141a08207b0d4236631d7
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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