Water → N-(4-Fluorophenyl)-N'-(4-{[2-(4-chlorobutyrylamino)-4-pyridyl]oxy}phenyl)urea

HRID 1010206Notes

Reaction equation

HRID 1010206 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)[CH:11]=[CH:10][N:9]=1)=[O:6].[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1.O1CCCC1.O>C(OCC)(=O)C>[F:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][C:12]3[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[CH:13]=3)=[CH:21][CH:20]=2)=[O:31])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 709554-Fluorophenyl isocyanateHCID 57933327HCID 57933327, compound

Product 1

HCID 22936908N-(4-Fluorophenyl)-N'-(4-{[2-(4-chlorobutyrylamino)-4-pyridyl]oxy}phenyl)urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-{[2-(4-Chlorobutyrylamino)-4-pyridyl]oxy}aniline (100 mg), p-fluorophenyl isocyanate (0.037 ml) and tetrahydrofuran (3 ml) were stirred at room temperature for 25 minutes. Water and ethyl acetate were added to the reaction solution for extraction, NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (hexane:ethyl acetate=1:1, followed by ethyl acetate and ethyl acetate:methanol=10:1). The solvent was distilled off under reduced pressure to obtain 56 mg of the target substance as a white solid.

Workup

  1. additionwas added to the extract
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with NH type silica gel, and column purification
  5. distillationThe solvent was distilled off under reduced pressure
  6. customto obtain 56 mg of the target substance as a white solid

Sources & evidence

ORD record
ord-1f117204a9d5478b9fb41d84a09c50c8
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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