Ethanol → HCID 68297595, compound

HRID 919839Notes

Reaction equation

HRID 919839 reaction equation
CCO.[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:32])=[C:10]2[C:15](=[CH:16][N:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](=[O:25])[C:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH:11]2)=[O:7]>C1COCC1.[Pd]>[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:32])=[C:10]2[C:15](=[CH:16][N:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13](=[O:25])[CH:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:11]2)=[O:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 682973581-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 68297595HCID 68297595, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 10% Pd/C (50 mg) and EtOH (5 mL) was added a solution of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (40 mg, 0.104 mmol) in 5 mL of THF. The resulting mixture was placed under H2 (35 psi) for 5 days. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc/hexanes+2% AcOH) to give 22 mg of the title compound as a white solid. MS: (+) m/z 389.34 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography (0-50% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-b8db267fa85d49e69a524aa1c498fd62
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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