2,4-Difluorophenyl isocyanate → N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chlorophenyl)-N'-(2,4-difluorophenyl)urea

HRID 1375766Notes

Reaction equation

HRID 1375766 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]([Cl:27])[CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[N:38]=[C:39]=[O:40]>C(Cl)(Cl)Cl>[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:39]([NH:38][C:32]4[CH:33]=[CH:34][C:35]([F:37])=[CH:36][C:31]=4[F:30])=[O:40])=[C:22]([Cl:27])[CH:21]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 226670624-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroaniline

Product 1

HCID 22667053N-(4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chlorophenyl)-N'-(2,4-difluorophenyl)ureaYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroaniline (260 mg) was dissolved in chloroform (10 ml). 2,4-Difluorophenyl isocyanate (198 mg) was then added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was purified by chromatography on silica gel by development with chloroform/acetone (10/1) to give 337 mg (yield 94%) of the title compound.

Workup

  1. customThe reaction solution was purified by chromatography on silica gel by development with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-69da5fd0a7614a3c963c33155a36decd
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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