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

HRID 388069Notes

Reaction equation

HRID 388069 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-dimethylphenyl]-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 stream. 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-101515c0a7764352bd31b7677c0628cc
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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