Ethyl Acetate → HCID 178512306, compound

HRID 1059453Notes

Reaction equation

HRID 1059453 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[NH:8][C:7]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O1CCCC1.CO>[C:9]([N:8]=[CH:7][NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[NH:8][C:7]=2[CH:16]=1)#[N:15]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18670209HCID 18670209, compound

Product 1

HCID 178512306HCID 178512306, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

500 mg of 8-aminomethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 400 mg of ethyl N2-cyanocarboxyimidate were dissolved in a solvent mixture of tetrahydrofuran (5 ml) with methanol (5 ml) and stirred at 40° C. for 1.5 hours. Then the reaction mixture was distributed into an aqueous solution of potassium carbonate and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) and recrystallized from methanol/ethyl acetate. Thus, 170 mg of the title compound was obtained as yellow crystals.

Workup

  1. extractionThe organic layer was extracted
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-44fa235d60f74aa5a6b79bf43495c38b
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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