Methanol → HCID 135674213, compound

HRID 1008332Notes

Reaction equation

HRID 1008332 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[F:22].[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33].CO>C(Cl)(Cl)Cl.CN(C)C=O>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[NH:31][C:32]([NH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[F:22])=[O:33]

Participants

6

Reactant 3

HCID 887MethanolHCID 5932582,4-Difluorophenyl isocyanateHCID 135674219HCID 135674219, compound

Product 1

HCID 135674213HCID 135674213, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

4-(4-Amino-3-fluorophenoxy)-6-methoxy-7-quinolinol (70 mg) was dissolved in chloroform (1.5 ml) and N,N-dimethylformamide (1 ml). 2,4-Difluorophenyl isocyanate (43 mg) was then added to the solution, and a reaction was allowed to proceed at room temperature for 3 hr. Methanol was added to the reaction solution. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (20/1) to quantitatively give the title compound.

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/methanol (20/1)

Sources & evidence

ORD record
ord-fc56150d18cf423880ac8201dda3c8e5
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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