Acetic Acid → HCID 67509239, compound

HRID 2201136Notes

Reaction equation

HRID 2201136 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([NH:17][C:18]3[CH:23]=[C:22]([NH:24][C:25]4[S:29][N:28]=[C:27]([CH3:30])[CH:26]=4)[C:21]([C:31]#[N:32])=[CH:20][C:19]=3[F:33])[C:14]([NH2:16])=[O:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].OO.CC(O)=[O:40]>CCO.CS(C)=O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([NH:17][C:18]3[C:19]([F:33])=[CH:20][C:21]([C:31]([NH2:32])=[O:40])=[C:22]([NH:24][C:25]4[S:29][N:28]=[C:27]([CH3:30])[CH:26]=4)[CH:23]=3)[C:14]([NH2:16])=[O:15])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67516101(R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)propanamide

Product 1

HCID 67509239HCID 67509239, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To a solution of (R)-3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)propanamide (9 mg, 0.019 mmol) in EtOH (1 mL) and DMSO (0.5 mL), aq. 1N NaOH (0.5 mL, 0.50 mmol) and aq. H2O2 (50%, 0.5 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (0.5 mL) was added. The mixture was purified by HPLC to give the titled compound (5 mg). MS 480.3 (M+H); UV 204.7, 292.8 nm.

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-32e0968d8af641d5814b17e613372912
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

Loading…