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

HRID 1817308Notes

Reaction equation

HRID 1817308 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[N:12][CH:11]=[C:10]([O:22][CH3:23])[C:9]=3[C:8]2=[O:24])=[CH:4][CH:3]=1.[C:27]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[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]([CH3:27])[S:18]([CH3:21])(=[O:20])=[O:19])=[N:12][CH:11]=[C:10]([O:22][CH3:23])[C:9]=3[C:8]2=[O:24])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 69063317N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]methanesulfonamide

Product 1

HCID 69065758N-[6-(4-Fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-1-yl]methanesulfonamide (0.097 g, 0.256 mmol) in DMF (2 mL) was added Cs2CO3 (0.083 g, 0.256 mmol) and MeI (0.04 g, 0.28 mmol, dissolved in DMF). After stirring for 2 hours, additional MeI (0.02 g, 0.14 mmol) was added. The product mixture was concentrated. The residue was partitioned between CHCl3 and pH 7 buffer. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound.

Workup

  1. concentrationThe product mixture was concentrated
  2. customThe residue was partitioned between CHCl3 and pH 7 buffer
  3. extractionThe organic extract
  4. dry with materialwas dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aa7549c08ed448aebbc07577d1bfa2c5
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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