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

HRID 1410829Notes

Reaction equation

HRID 1410829 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-f616a42d176c4fa0bc7d99be2d82cd73
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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