4-Fluorophenyl isocyanate → N-[4-(2-Butylaminopyridin-4-yl)oxyphenyl]-N'-(4-fluorophenyl)urea
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
Product 1
Reagents, catalysts & solvents 1
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
- additionAfter adding NH type silica gel to the reaction solution
- distillationthe solvent was distilled off under reduced pressure
- additionThe silica gel was charged into a dry column
- custompacked with NH type silica gel, and column purification
- distillationwas distilled off under reduced pressure
- customto obtain 15 mg of the target substance as a light yellow powder
Sources & evidence
- ORD record
- ord-d2e463b7bcd74865b0edf6fc0ad757a4
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253286B2
Reaction notes
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