Acetic Acid → HCID 69284981, compound

HRID 2201131Notes

Reaction equation

HRID 2201131 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][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[C:18]([NH2:20])=[O:19])=[C:5]([F:34])[CH:4]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:41]>CCO.CS(C)=O>[NH2:20][C:18](=[O:19])[C@H:17]([NH:16][C:6]1[C:5]([F:34])=[CH:4][C:3]([C:1]([NH2:2])=[O:41])=[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]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67509932HCID 67509932, compound

Product 1

HCID 69284981HCID 69284981, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

To a solution of (R)-2-(4-cyano-2-fluoro-5-(3-methylisothiazol-5-ylamino)phenylamino)-3-(4-(pyridin-4-yl)phenyl)propanamide (12 mg, 0.025 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 (6 mg). MS 491.1 (M+H); UV 216.8, 278.0, 312.5 nm.

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-4fd6cbb186524a6cb1eeb454e5feec1a
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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