Water → HCID 18670347, compound

HRID 1059437Notes

Reaction equation

HRID 1059437 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]2[S:24][C:23]3[N:25]=[CH:26][CH:27]=[N:28][C:22]=3[N:21]([CH2:29][O:30][CH3:31])[C:20]=2[CH:32]=1.O>CC(C)=O.C(OCC)(=O)C>[CH3:31][O:30][CH2:29][N:21]1[C:20]2[CH:32]=[C:16]([CH2:15][NH:14][C:2]([NH:3][C:5](=[O:12])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[S:1])[CH:17]=[CH:18][C:19]=2[S:24][C:23]2[N:25]=[CH:26][CH:27]=[N:28][C:22]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 186704238-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Product 1

HCID 18670347HCID 18670347, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 5 ml of a solution of 350 mg of ammonium thiocyanate in acetone was added in a nitrogen atmosphere 0.50 ml of benzoyl chloride and the resulting mixture was heated under reflux for 5 minutes. Then 5 ml of a solution of 890 mg of 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine in acetone was added thereto and the resulting mixture was heated under reflux for additional 1.5 hours. Next, the reaction mixture was distributed into water and ethyl acetate, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) and recrystallized from diisopropyl ether to thereby give 710 mg of the title compound as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 minutes
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for additional 1.5 hours
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3729305e54ce418db71fb544fee98c2a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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