Ethanol → 1-Benzyl-5-hydroxy-2-oxo-3-phenethyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

HRID 919683Notes

Reaction equation

HRID 919683 reaction equation
CCO.[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:34])=[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]#[C:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:11]2)=[O:7]>[Pd].CCOC(C)=O.CO>[CH3:4][O:5][C:6]([C:8]1[C:9]([OH:34])=[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]([CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[CH:11]2)=[O:7]

Participants

5

Reactant 2

HCID 702EthanolHCID 682975811-Benzyl-5-hydroxy-2-oxo-3-phenylethynyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 682974661-Benzyl-5-hydroxy-2-oxo-3-phenethyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl esterYield 59.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A flask was charged with 10% palladium on carbon (100 mg), EtOH (10 mL), and a solution of 1-benzyl-5-hydroxy-2-oxo-3-phenylethynyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (250 mg, 0.61 mmol) in 10 mL of EtOAc/MeOH (1:1). The mixture was placed under H2 atmosphere and stirred for 16 h. After removal of Pd/C by filtration, the solution was concentrated in vacuo. The residue was purified by silica gel chromatography (0-60% EtOAc/hexanes+2% AcOH) to give 150 mg of the title compound as an off-white solid. MS: (+) m/z 415.12 (M+1).

Workup

  1. customAfter removal of Pd/C
  2. filtrationby filtration
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (0-60% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-aabdbe78fe7f4050ba1ceea5222f610d
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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