Acetic Acid → 1-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-acetylamino-ethyl)-amide

HRID 1410818Notes

Reaction equation

HRID 1410818 reaction equation
CO[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][N:6]=1)=[O:4].[NH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:30])[CH3:29].CC(O)=O.O>CCO.CCOC(C)=O>[C:28]([NH:27][CH2:26][CH2:25][NH:24][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:7][N:6]=1)=[O:4])(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 66082N-(2-aminoethyl)acetamideHCID 682971941-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

Product 1

HCID 867141231-Benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-acetylamino-ethyl)-amideYield 64.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzyl-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (20 mg, 0.065 mmol) and N-(2-amino-ethyl)-acetamide (20 mg, 0.19 mmol) in EtOH (3 mL) was refluxed for 16 h. After cooling to r.t., AcOH (0.1 mL), water (15 mL) and EtOAc (20 mL) were added. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography (0-7% MeOH/CH2Cl2) to give 16 mg of the title compound as a light yellow solid. MS: (+) m/z 381.34 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (0-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b77c1e11086f40abb37edbb2e105b7e0
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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