Methanesulfonyl chloride → N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]methanesulfonamide

HRID 1817307Notes

Reaction equation

HRID 1817307 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:7]2=[O:14].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:6]2[CH2:5][CH2:4][C:3]3[C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[N:11][CH:10]=[C:9]([O:12][CH3:13])[C:8]=3[C:7]2=[O:14])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 690622305-amino-2-(4-fluorobenzyl)-8-methoxy-3,4-dihydro-2,6-naphthyridin-1(2H)-one

Product 1

HCID 69063317N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-2-(4-fluorobenzyl)-8-methoxy-3,4-dihydro-2,6-naphthyridin-1(2H)-one (0.889 g, 2.95 mmol) in pyridine (5 mL) was added dropwise methanesulfonyl chloride (0.575 g, 5.016 mmol). After stirring for an hour at room temperature, the product mixture was quenched with pH 7 buffer, then concentrated under vacuum. The residue was dissolved in CHCl3 and pH 7 buffer, the pH of the aqueous layer was adjusted to pH 5 with 1N NaOH and the layers separated. Several more extractions with CHCl3 were performed. The organic extracts were dried with Na2SO4, filtered, and concentrated under vacuum, then dissolved in toluene and CHCl3 and evaporated to provide the title compound.

Workup

  1. customthe product mixture was quenched with pH 7 buffer
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in CHCl3
  4. customthe layers separated
  5. extractionSeveral more extractions with CHCl3
  6. dry with materialThe organic extracts were dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. dissolutiondissolved in toluene
  10. customCHCl3 and evaporated

Sources & evidence

ORD record
ord-4ff67db41445447ab4fd0339d1e43d91
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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