Methyl iodide → HCID 69061292, compound

HRID 1817361Notes

Reaction equation

HRID 1817361 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:23][CH3:24])[C:10](=[O:22])[N:11]([CH3:21])[C:12]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:7]1=[O:25].[H-].[Na+].I[CH3:33]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([O:23][CH3:24])[C:10](=[O:22])[N:11]([CH3:21])[C:12]=2[N:16]([CH3:33])[S:17]([CH3:20])(=[O:18])=[O:19])[C:7]1=[O:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69062327HCID 69062327, compound

Product 1

HCID 69061292HCID 69061292, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A cold (0° C.) solution of N-[6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-methyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-1-yl]methanesulfonamide (60 mg, 0.14 mmol) in anhydrous DMF (1 mL) was treated with sodium hydride (6.8 mg, 0.17 mmol; 60% dispersion in oil). The resultant mixture was stirred at the same temperature for 30 minutes, and treated with iodomethane (38 mg, 0.27 mmol). The reaction mixture was allowed to slowly warmed up to room temperature. The product mixture was concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound. ES MS M+1=458

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between chloroform and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-30f5643aad2e4cb68ecae45516401adb
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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