Acetic Acid → HCID 68297178, compound

HRID 919794Notes

Reaction equation

HRID 919794 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-eba5c1be09ff4290bdded5916bb6c14e
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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