Ethyl Acetate → N-(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)formamide

HRID 1059428Notes

Reaction equation

HRID 1059428 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[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.[Cl-].[NH4+].[C:22](OCC)(=[O:24])C>C(OCC)=O>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][NH:1][CH:22]=[O:24])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 186704238-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 18670704N-(10-Methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)formamide

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

250 mg of 8-aminomethyl-10-methoxymethyl-10H-pyrazino-[2,3-b][1,4]benzothiazine was heated under reflux in 10 ml of ethyl formate for 3 hours. Then the reaction mixture was brought back to room temperature and distributed into an aqueous solution of ammonium chloride and ethyl acetate. The organic layer was extracted, washed with water and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were filtered after adding diisopropyl ether. Thus 230 mg of the title compound was obtained as yellow crystals.

Workup

  1. customwas brought back to room temperature
  2. extractionThe organic layer was extracted
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe crystals thus precipitated
  7. filtrationwere filtered
  8. additionafter adding diisopropyl ether

Sources & evidence

ORD record
ord-6bcd6d99c1284dc083c71cbdc7f88f67
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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