4-Fluorophenyl isocyanate → Ethyl(E)-3-[2-amino-4-(4-{[(4-fluoroanilino)carbonyl]amino}phenoxy)-3-pyridyl]-2-propenoate

HRID 387801Notes

Reaction equation

HRID 387801 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=2)[CH:5]=[CH:4][N:3]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>O1CCCC1>[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:6]([O:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)=[O:32])=[CH:20][CH:21]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 58931285Ethyl(E)-3-[2-amino-4-(4-aminophenoxy)-3-pyridyl]-propenoate

Product 1

HCID 57933326Ethyl(E)-3-[2-amino-4-(4-{[(4-fluoroanilino)carbonyl]amino}phenoxy)-3-pyridyl]-2-propenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl(E)-3-[2-amino-4-(4-aminophenoxy)-3-pyridyl]-2-propenoate (230 mg), p-fluorophenyl isocyanate (0.11 ml) and tetrahydrofuran (6 ml) were stirred at room temperature for 30 minutes. 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 (ethyl acetate). The solvent was distilled off under reduced pressure to obtain 200 mg of a white solid.

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

Sources & evidence

ORD record
ord-ab0c1504416d4a44964a4ddc9abbcdfd
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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