Methanol → N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl)oxy}-2,3-dimethylphenyl)-N'-(2,4-difluorophenyl)urea

HRID 1375768Notes

Reaction equation

HRID 1375768 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([CH3:27])[C:21]=3[CH3:28])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[N:39]=[C:40]=[O:41].CO>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH:24][C:40]([NH:39][C:33]4[CH:34]=[CH:35][C:36]([F:38])=[CH:37][C:32]=4[F:31])=[O:41])=[C:22]([CH3:27])[C:21]=3[CH3:28])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5932582,4-Difluorophenyl isocyanateHCID 226671504-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylaniline

Product 1

HCID 22667195N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl)oxy}-2,3-dimethylphenyl)-N'-(2,4-difluorophenyl)ureaYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylaniline (260 mg) was dissolved in N,N-dimethylformamide (5 ml). 2,4-Difluorophenyl isocyanate (121 mg) was then added to the solution, and a reaction was allowed to proceed at room temperature overnight. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was washed with methanol and was collected by filtration to give 219 mg (yield 61%) of the title compound.

Workup

  1. customthe solvent was removed by distillation under the reduced pressure
  2. washThe residue was washed with methanol
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b29223f98a394c5583aa53f31d3f7c6f
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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