1,1'-Carbonyldiimidazole → N-(Methanesulfonyl)-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetamide

HRID 1059439Notes

Reaction equation

HRID 1059439 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][C:16]([OH:18])=O)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:31][S:32]([NH2:35])(=[O:34])=[O:33]>O1CCCC1>[CH3:31][S:32]([NH:35][C:16](=[O:18])[CH2:15][C:12]1[CH:13]=[CH:14][C:7]2[S:6][C:5]3[N:4]=[CH:3][CH:2]=[N:1][C:10]=3[NH:9][C:8]=2[CH:11]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 1867013310H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetic acid

Product 1

HCID 18670435N-(Methanesulfonyl)-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetamideYield 48.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.259 g of (10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetic acid in tetrahydrofuran (10 ml) was added in a nitrogen atmosphere 0.18 g of carbonyldiimidazole and the resulting mixture was heated under reflux for 30 minutes. Then the reaction mixture was brought back to room temperature and 0.285 g of methanesulfonamide was added thereto. After stirring at room temperature for 16 hours, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.163 g of the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customwas brought back to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-c35e80f992534b5a97d09881c7296d8b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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