Potassium Carbonate → 3-[(2,4-Dimethoxybenzyl)amino]-5-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]isothiazole-4-carboxamide

HRID 871034Notes

Reaction equation

HRID 871034 reaction equation
[C:1]([C:3]1[C:4]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])=[N:5][S:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=2[F:25])=[O:16])=[CH:10][CH:9]=1)#[N:2].C([O-])([O-])=[O:39].[K+].[K+]>CS(C)=O.OO.[Cl-].[Na+].O>[CH3:37][O:36][C:29]1[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=1[CH2:27][NH:26][C:4]1[C:3]([C:1]([NH2:2])=[O:39])=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=3[F:25])=[O:16])=[CH:10][CH:9]=2)[S:6][N:5]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 866892251-(4-{4-Cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

Product 1

HCID 716208403-[(2,4-Dimethoxybenzyl)amino]-5-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]isothiazole-4-carboxamideYield 91%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-(4-{4-cyano-3-[(2,4-dimethoxybenzyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea (26 mg, 0.050 mmol) in 0.8 mL DMSO at rt was added catalytic K2CO3, 5 drops 30% hydrogen peroxide and the reaction stirred at rt for 30 min. The reaction was added into a solution of dilute brine and the precipitant filtered and rinsed with water, then 30% EtOAc/hexane to give the title compound as a pale yellow solid (24 mg, 91%).

Workup

  1. filtrationthe precipitant filtered
  2. washrinsed with water

Sources & evidence

ORD record
ord-6521b77b6c8d495d99ad68eaa8f91b77
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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