Acetic Anhydride → methyl 6-[(4-fluorophenyl)methyl]-4-hydroxy-3,5-dioxo-7,8-dihydro-2H-2,6-naphthyridine-1-carboxylate

HRID 1817296Notes

Reaction equation

HRID 1817296 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:22])[CH:11]=[N+:12]([O-])[C:13]=3[C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:23])=[CH:4][CH:3]=1.C(OC(=O)C)(=[O:28])C.C[O-].[Na+]>>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:22])[C:11](=[O:28])[NH:12][C:13]=3[C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:23])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10942334Sodium MethoxideHCID 69058416Methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

Product 1

HCID 54692262methyl 6-[(4-fluorophenyl)methyl]-4-hydroxy-3,5-dioxo-7,8-dihydro-2H-2,6-naphthyridine-1-carboxylate

Procedure

To methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide (0.178 g, 0.514 mmol) was added acetic anhydride (0.157 g, 1.542 mmol) and refluxed. After 1 hour, the reaction mixture was concentrated under vacuum, then sodium methoxide (30 wt. % in methanol, 0.083 g, 1.540 mmol) was added. After stirring at room temperature for 1 hour, the product mixture was concentrated under vacuum. The residue was purified by reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound as a pale yellow solid.

Workup

  1. temperaturerefluxed
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. concentrationthe product mixture was concentrated under vacuum
  4. customThe residue was purified by reverse phase HPLC
  5. washeluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA)

Sources & evidence

ORD record
ord-d9a42cfcda9c4bf4a04963e6c0bce904
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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