4-Fluorophenyl isocyanate → N-[4-(2-aminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

HRID 1433582Notes

Reaction equation

HRID 1433582 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>O1CCCC1.CN(C)C=O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)=[O:25])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 229367412-Amino-4-(4-aminophenoxy)pyridine

Product 1

HCID 22936644N-[4-(2-aminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 0.53 g of 2-amino-4-(4-aminophenoxy)pyridine in a mixture of 20 ml of tetrahydrofuran and 10 ml of dimethylformamide, 0.36 ml of p-fluorophenyl isocyanate was added and the mixture was stirred for 1 hour. NH type silica gel was added to the reaction solution, 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 (chloroform:methanol=20:1, followed by 10:1). The solvent was distilled off under reduced pressure to obtain 610 mg of the target substance as a white powder.

Workup

  1. additionwas added
  2. additionNH type silica gel was added to the reaction solution
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe silica gel was charged into a dry column
  5. custompacked with NH type silica gel, and column purification
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto obtain 610 mg of the target substance as a white powder

Sources & evidence

ORD record
ord-6825a077530840b9a6b21e62afaa457d
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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