HCID 86605630, compound → HCID 86605644, compound

HRID 1986466Notes

Reaction equation

HRID 1986466 reaction equation
[NH2:1][C:2](=[O:35])/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1>CO.O1CCCC1.[C].[Pd]>[NH2:1][C:2](=[O:35])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[C:8]2[C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1

Participants

5

Reactant 1

HCID 86605630HCID 86605630, compound

Product 1

HCID 86605644HCID 86605644, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl {[6-[(1E)-3-amino-3-oxoprop-1-en-1-yl]-2-isobutyl-4-(4-methylphenyl)-quinolin-3-yl]methyl}carbamate (250 mg, 0.53 mmol) in methanol (5 ml) and tetrahydrofuran (5 ml) was added 5% palladium-carbon (0.10 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 12 hrs. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give tert-butyl {[6-(3-amino-3-oxopropyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (204 mg, yield 81%) as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e99460fbf7634c10a2bebaba1ca3adb6
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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