Methanol → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(3-fluoro-2-methoxyphenyl)urea

HRID 1008366Notes

Reaction equation

HRID 1008366 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].ClC(Cl)(O[C:29](=O)[O:30][C:31](Cl)(Cl)Cl)Cl.[F:37][C:38]1C=CC=[C:40](OC)[C:39]=1N.C[OH:48].C([N:51]([CH2:54]C)[CH2:52][CH3:53])C>C(Cl)(Cl)Cl.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:54]([NH:51][C:52]2[CH:53]=[CH:40][CH:39]=[C:38]([F:37])[C:29]=2[O:30][CH3:31])=[O:48])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

8

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 94429TriphosgeneHCID 4592532-Fluoro-6-methoxyanilineHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 22667166N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(3-fluoro-2-methoxyphenyl)ureaYield 13%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (120 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (110 mg) in dichloromethane was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, 3-fluoro-o-anisidine (132 μl) was added to the reaction solution, and the mixture was stirred at room temperature for 2 hr. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with chloroform/methanol (91/9) to give 23 mg (yield 13%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. customthe solvent was removed by distillation under the reduced pressure
  3. customThe residue was purified by chromatography on silica gel by development with chloroform/methanol (91/9)

Sources & evidence

ORD record
ord-2450a0f36b3d496194d0326ca6f08f3f
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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