Acetic Acid → HCID 86714121, compound

HRID 919809Notes

Reaction equation

HRID 919809 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29].CC(O)=O.O>CCO>[C:28]([NH:27][CH2:26][CH2:25][NH:24][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4])(=[O:30])[CH3:29]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 66082N-(2-aminoethyl)acetamideHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 86714121HCID 86714121, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (20 mg, 0.065 mmol) and N-(2-amino-ethyl)-acetamide (20 mg, 0.19 mmol), in EtOH (2 mL) was refluxed for 16 h. After cooling to r.t., AcOH (0.1 mL) and water (20 mL) were added. The resulting cloudy solution was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 13 mg of the title compound as an off-white solid. MS: (+) m/z 381.34 (M+1).

Workup

  1. extractionThe resulting cloudy solution was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4c2e753c353a4008896c3a4a5308dee7
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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