Methyl iodide → HCID 22272646, compound

HRID 1064809Notes

Reaction equation

HRID 1064809 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([NH:24][C:25]2[C:30]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[C:27]([OH:34])[C:26]=2[CH:35]([CH3:37])[CH3:36])=[O:23])[CH2:17][CH2:16]1.I[CH3:39]>CN(C=O)C.O>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[S:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]([NH:24][C:25]2[C:30]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:28]=[C:27]([O:34][CH3:39])[C:26]=2[CH:35]([CH3:37])[CH3:36])=[O:23])[CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222726162-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide

Product 1

HCID 22272646HCID 22272646, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydride (21 mg, 0.48 mmol) was added to a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (200 mg, 0.40 mmol) in DMF (2 ml), the mixture was stirred at 40° C. for 10 minutes and iodomethane (68 mg, 0.48 mmol) was added thereto followed by stirring for 1 hour. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=50:1) to provide 47 mg (yield 23%) of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]-piperazin-1-yl]-N-(2,6diisopropyl-3-methoxyphenyl)acetamide. This was made into a dihydrochloride and recrystallized to provide the desired compound as colorless powdery crystals.

Workup

  1. stirringby stirring for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-6da1f4b7bd044211b5b1008feb48968f
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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