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

HRID 387923Notes

Reaction equation

HRID 387923 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-0b1672bceb1c4ff4875790ae7f121181
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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