Water → HCID 18670322, compound

HRID 1059406Notes

Reaction equation

HRID 1059406 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)(O)[CH3:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:23]=[CH:24][CH:25]=[N:26][C:5]1=2.ClS(OC)(=O)=O.O.C(OCC)(=O)C>ClCCl>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]([C:11]2[CH:12]=[CH:13][C:8]3[S:7][C:6]4[N:23]=[CH:24][CH:25]=[N:26][C:5]=4[N:4]([CH2:3][O:2][CH3:1])[C:9]=3[CH:10]=2)=[CH2:15])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 69938Methyl chlorosulphateHCID 18670441HCID 18670441, compound

Product 1

HCID 18670322HCID 18670322, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 303 mg of 1-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)1-(pyridin-3-yl)ethanol in dichloromethane was added in a nitrogen atmosphere 0.32 ml of methyl chlorosulfonate and the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 230 mg of the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customwas brought back to room temperature
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-03dc200643aa4ec2bda2b17c98c9faf0
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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