Ethanol → N-[6-(4-Fluorobenzyl)-4-methoxy-2-oxido-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide

HRID 1817309Notes

Reaction equation

HRID 1817309 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[N:12][CH:11]=[C:10]([O:23][CH3:24])[C:9]=3[C:8]2=[O:25])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1.C(O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[N+:12]([O-:36])[CH:11]=[C:10]([O:23][CH3:24])[C:9]=3[C:8]2=[O:25])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 70297m-Chloroperbenzoic acidHCID 69065758N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide

Product 1

HCID 69058516N-[6-(4-Fluorobenzyl)-4-methoxy-2-oxido-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide (0.35 g, 0.89 mmol) in CH2Cl2 (10 mL) was added mCPBA (1.08 g, 6.23 mmol) in portions. After stirring for 3.5 hours at reflux, the product mixture was cooled to room temperature, 1 mL of ethanol was added, and the solution was concentrated. The residue was partitioned between CHCl3 and saturated Na2SO3. The organic layer was extracted repeatedly with saturated sodium bicarbonate. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the crude title compound.

Workup

  1. temperatureat reflux
  2. concentrationthe solution was concentrated
  3. customThe residue was partitioned between CHCl3 and saturated Na2SO3
  4. extractionThe organic layer was extracted repeatedly with saturated sodium bicarbonate
  5. extractionThe organic extract
  6. dry with materialwas dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4d858c0c2ff940d695cbb2c96147b6ca
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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