Acetic Acid → HCID 68297178, compound

HRID 1410797Notes

Reaction equation

HRID 1410797 reaction equation
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:27])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[O:25][CH3:26])[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=1.CC(O)=O.O>CCO>[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][NH:34][C:3]([C:5]2[N:6]=[CH:7][C:8]3[C:9](=[O:27])[N:10]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=4[O:25][CH3:26])[CH:11]=[CH:12][C:13]=3[C:14]=2[OH:15])=[O:4])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 673264-FluorobenzylamineHCID 682972407-(2,4-Dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Product 1

HCID 68297178HCID 68297178, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-(2,4-dimethoxy-benzyl)-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (15 mg, 0.041 mmol) and 4-fluorobenzylamine (0.020 mL, 0.14 mmol) in EtOH (2 mL) was refluxed for 16 h. After cooling the mixture to r.t., AcOH (0.1 mL) and water (2 mL) were added. The resulting precipitate was isolated by filtration, washed with cold MeOH/H2O (5 mL, 1:1), and purified by silica gel chromatography (0-2% MeOH/CH2Cl2) to give 15 mg of the title compound. MS: (+) m/z 464.35 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with cold MeOH/H2O (5 mL, 1:1)
  4. custompurified by silica gel chromatography (0-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-47ee8b387f9e4f6fb20ee486c3d6276c
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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