Potassium Carbonate → HCID 17819617, compound

HRID 1375810Notes

Reaction equation

HRID 1375810 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([OH:32])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)=[CH:15][C:14]=1[F:33])=[O:11].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(=O)([O-])O.[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH2:42][CH2:43][N:44]4[CH2:49][CH2:48][O:47][CH2:46][CH2:45]4)=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)=[CH:15][C:14]=1[F:33])=[O:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 135674213HCID 135674213, compound

Product 1

HCID 17819617HCID 17819617, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

N-(2,4-Difluorophenyl)-N′-{2-fluoro-4-[(7-hydroxy-6-methoxy-4-quinolyl)oxy)phenyl}urea (20 mg), potassium carbonate (7 mg), tetra-n-butylammonium iodide (2 mg), and N-(2-chloroethyl)morpholine hydrochloride (10 mg) were dissolved in N,N-dimethylformamide (1 ml), and the solution was stirred at 70° C. overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (30/1) to give 14 mg (yield 57%) of the title compound.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (30/1)

Sources & evidence

ORD record
ord-8f733c70b9ec4182a97eb5d3c049bf40
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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