Methyl iodide → HCID 22711393, compound

HRID 352894Notes

Reaction equation

HRID 352894 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:27][C:28](=[O:34])[NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=O)(C)(C)C.[C:35](=O)(O)[O-].[Na+].CI.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>CN(C)C=O.ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[Cl:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:27][C:28](=[O:34])[N:29]([CH3:35])[S:30]([CH3:33])(=[O:32])=[O:31])[CH2:10]1)(=[O:15])=[O:16])=[CH:25]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22709915HCID 22709915, compound

Product 1

HCID 22711393HCID 22711393, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In N,N-dimethylformamide (10 ml) was dissolved 1-tert-butoxycarbonyl-4-[(5-chloroindol-2-yl)sulfonyl]-2-[(N-methylsulfonylcarbamoyl)methyl]piperazine (347 mg), followed by the addition of sodium bicarbonate (55 mg) and methyl iodide (0.05 ml). The resulting mixture was stirred overnight at room temperature. The reaction mixture was then concentrated under reduced pressure. Dichloromethane was added to the residue and the resulting mixture was washed successively with water and saturated aqueous NaCl solution, each once. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (Φ1.7×12.0 cm, dichloromethane:methanol=200:1), whereby the title compound was obtained as colorless foam. The resulting foam was dissolved in dichloromethane (1 ml), followed by the addition of trifluoroacetic acid (2 ml). After the resulting mixture was stirred at room temperature for 1 minute, the reaction mixture was concentrated under reduced pressure. Diethyl ether was added to the residue and the precipitate so formed was collected by filtration, whereby the title compound (189 mg, 43%) was obtained as colorless foam.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionDichloromethane was added to the residue
  3. washthe resulting mixture was washed successively with water and saturated aqueous NaCl solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (Φ1.7×12.0 cm, dichloromethane:methanol=200:1), whereby the title compound
  8. customwas obtained as colorless foam
  9. stirringAfter the resulting mixture was stirred at room temperature for 1 minute
  10. concentrationthe reaction mixture was concentrated under reduced pressure
  11. additionDiethyl ether was added to the residue
  12. customthe precipitate so formed
  13. filtrationwas collected by filtration, whereby the title compound (189 mg, 43%)
  14. customwas obtained as colorless foam

Sources & evidence

ORD record
ord-74bf29c9f3e84e1b8adfb9ff157b65a4
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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