N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethylphenyl]-N'-cyclopropylurea → HCID 135829394, compound

HRID 1433731Notes

Reaction equation

HRID 1433731 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH:30]4[CH2:32][CH2:31]4)=[O:28])=[C:22]([CH3:33])[C:21]=3[CH3:34])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:35]#[N:36])C1C=CC=CC=1>[C].[Pd].O1CCCC1>[CH3:33][C:22]1[C:21]([CH3:34])=[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([C:35]#[N:36])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)[CH:25]=[CH:24][C:23]=1[NH:26][C:27]([NH:29][CH:30]1[CH2:31][CH2:32]1)=[O:28]

Participants

4

Reactant 1

HCID 22936500N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethylphenyl]-N'-cyclopropylurea

Product 1

HCID 135829394HCID 135829394, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding N-[4-(7-benzyloxy-6-cyanoquinolin-4-yloxy)-2,3-dimethyl phenyl]-N′-cyclopropylurea (1600 mg) to tetrahydrofuran (400 ml), palladium-carbon (2000 mg) was further added and the mixture was stirred overnight at room temperature under a hydrogen atmosphere. The palladium-carbon was removed by filtration, washing was performed with dimethylformamide, and the filtrate was concentrated under reduced pressure to obtain the title compound (827 mg).

Workup

  1. additionwas further added
  2. customThe palladium-carbon was removed by filtration
  3. washwashing
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-76cc49a663114bb3b0ba04ec78ca033e
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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