Methyl iodide → HCID 23565218, compound

HRID 1059411Notes

Reaction equation

HRID 1059411 reaction equation
CI.[N:3]1[C:12]2[NH:11][C:10]3[CH:13]=[C:14]([CH:17]([OH:21])[C:18]([OH:20])=[O:19])[CH:15]=[CH:16][C:9]=3[S:8][C:7]=2[N:6]=[CH:5][CH:4]=1.[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][O:19][C:18](=[O:20])[CH:17]([C:14]1[CH:15]=[CH:16][C:9]2[S:8][C:7]3[N:6]=[CH:5][CH:4]=[N:3][C:12]=3[NH:11][C:10]=2[CH:13]=1)[OH:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18670331HCID 18670331, compound

Product 1

HCID 23565218HCID 23565218, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg of methyl iodide was added to a solution of 100 mg of (10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)hydroxyacetic acid in N,N-dimethylformamide (8 ml) in the presence of 260 mg of potassium carbonate. After purifying by silica gel column chromatography (eluted with dichloromethane/methanol) and recrystallizing from ethyl acetate/diisopropyl ether, 68 mg of the title compound was obtained as yellow crystals.

Workup

  1. customAfter purifying by silica gel column chromatography (eluted with dichloromethane/methanol)
  2. customrecrystallizing from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-9256be13364447ddb198c520cf324e5a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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