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

HRID 387790Notes

Reaction equation

HRID 387790 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:8]=2)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>O1CCCC1>[CH2:14]([NH:13][C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:18]=[CH:19][C:2]([NH:1][C:28]([NH:27][C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)=[O:29])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 229369234-(4-Aminophenoxy)-2-butylaminopyridine

Product 1

HCID 22936554N-[4-(2-Butylaminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Aminophenoxy)-2-butylaminopyridine (54 mg), p-fluorophenyl isocyanate (34.5 mg) and tetrahydrofuran (5 ml) were stirred at room temperature for 2.5 hours. After adding NH type silica gel 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 (hexane:ethyl acetate=1:1, followed by ethyl acetate). The solvent was distilled off under reduced pressure and the residue was solidified with ethyl acetate-hexane to obtain 15 mg of the target substance as a light yellow powder.

Workup

  1. additionAfter adding NH type silica gel to the reaction solution
  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 15 mg of the target substance as a light yellow powder

Sources & evidence

ORD record
ord-4858a649d51248c2bf54cfc3c258203c
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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