Water → N-(4-Fluorophenyl)-N'-(4-{[2-(2-oxotetrahydro-1H-1-pyrrolyl)-4-pyridyl]oxy}phenyl)urea

HRID 387817Notes

Reaction equation

HRID 387817 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29]Cl)[CH:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.O>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][C:26]4=[O:31])[CH:20]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22936908N-(4-Fluorophenyl)-N'-(4-{[2-(4-chlorobutyrylamino)-4-pyridyl]oxy}phenyl)urea

Product 1

HCID 22936528N-(4-Fluorophenyl)-N'-(4-{[2-(2-oxotetrahydro-1H-1-pyrrolyl)-4-pyridyl]oxy}phenyl)ureaYield 40.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Fluorophenyl)-N′-(4-{[2-(4-chlorobutyrylamino)-4-pyridyl]oxy}phenyl)urea (56 mg), potassium carbonate (46 mg) and dimethylformamide (2 ml) were stirred at 150° C. for 15 minutes. Water and ethyl acetate were added for extraction, and the extract was passed through a glass filter coated with silica gel. The silica gel was washed with ethyl acetate, and the organic layer was distilled off under reduced pressure. Ethyl acetate and hexane were added to the residue, and the precipitated solid was filtered out to obtain 21 mg of a faint brown powder.

Workup

  1. filtrationfilter
  2. washThe silica gel was washed with ethyl acetate
  3. distillationthe organic layer was distilled off under reduced pressure
  4. additionEthyl acetate and hexane were added to the residue
  5. filtrationthe precipitated solid was filtered out

Sources & evidence

ORD record
ord-9c5c50da28fc46bfb2a8a9c6f38c0721
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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