Methyl iodide → HCID 19357005, compound

HRID 377906Notes

Reaction equation

HRID 377906 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].I[CH3:33]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]([CH3:33])[C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[C:22]([O:28][CH3:29])[CH:23]=[C:24]([O:26][CH3:27])[CH:25]=3)[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 17893214HCID 17893214, compound

Product 1

HCID 19357005HCID 19357005, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(100 mg, 0.25 mmol) was dissolved in dimethylformamide(15 ml) and thereto sodium hydride(6.0 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 15 min and thereto iodomethane(35 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 16 hrs, concentrated under the reduced pressure to remove dimethylformamide, and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 hrs
  2. concentrationconcentrated under the reduced pressure
  3. customto remove dimethylformamide
  4. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-0448c25dbbe3436981065a003812d77f
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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