Potassium Carbonate → 5-[4-({[(2-Fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]-3-[(3-morpholin-4-ylpropyl)amino]isothiazole-4-carboxamide

HRID 871033Notes

Reaction equation

HRID 871033 reaction equation
[C:1]([C:3]1[C:4]([NH:26][CH2:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[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:37].[K+].[K+]>CS(C)=O.OO.[Cl-].[Na+].O>[F:25][C:19]1[CH:20]=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=1[NH:17][C:15]([NH:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[S:6][N:5]=[C:4]([NH:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[C:3]=2[C:1]([NH2:2])=[O:37])=[CH:9][CH:10]=1)=[O:16]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 866892371-(4-{4-Cyano-3-[(3-morpholin-4-ylpropyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea

Product 1

HCID 716230295-[4-({[(2-Fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]-3-[(3-morpholin-4-ylpropyl)amino]isothiazole-4-carboxamideYield 85%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 1-(4-{4-cyano-3-[(3-morpholin-4-ylpropyl)amino]isothiazol-5-yl}phenyl)-3-(2-fluoro-5-methylphenyl)urea (5 mg, 0.011 mmol) in 0.8 mL DMSO at rt was added catalytic K2CO3, 1 drop 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 20% EtOAc/hexane. The product was washed from the filter paper using 15% MeOH/CHCl3 and then evaporated to give the title compound as a white solid (5 mg, 85%).

Workup

  1. filtrationthe precipitant filtered
  2. washrinsed with water
  3. washThe product was washed from the filter paper
  4. customevaporated

Sources & evidence

ORD record
ord-ae0aadce62b14e1bab526cfddb2d4945
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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