Acetic Acid → 1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (2-acetylamino-ethyl)-amide

HRID 919823Notes

Reaction equation

HRID 919823 reaction equation
CO[C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:8]2)=[O:4].[NH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:36])[CH3:35].CC(O)=O>CCO>[C:34]([NH:33][CH2:32][CH2:31][NH:30][C:3]([C:5]1[C:6]([OH:29])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:8]2)=[O:4])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66082N-(2-aminoethyl)acetamideHCID 682973581-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Product 1

HCID 601514011-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid (2-acetylamino-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (25 mg, 0.065 mmol) and N-(2-amino-ethyl)-acetamide in EtOH (3 mL) was refluxed for 48 h. After cooling to r.t., AcOH (0.1 mL) was added, and solvent was evaporated in vacuo. The residue was purified by silica gel chromatography (0-3% MeOH/CH2Cl2) to give 12 mg of the title compound as a light yellow solid. MS: (+) m/z 457.35 (M+1).

Workup

  1. temperaturewas refluxed for 48 h
  2. customsolvent was evaporated in vacuo
  3. customThe residue was purified by silica gel chromatography (0-3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-416ece8027784c8380bca85c7081c541
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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