Hydrochloric Acid → HCID 18670389, compound

HRID 1059431Notes

Reaction equation

HRID 1059431 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][CH2:15][C:16]#[N:17])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:18]=[CH:19][CH:20]=[N:21][C:5]1=2.[OH-].[K+].Cl.C(OCC)(=[O:27])C>CS(C)=O>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][CH2:15][C:16]([NH2:17])=[O:27])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:18]=[CH:19][CH:20]=[N:21][C:5]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 18670532HCID 18670532, compound

Product 1

HCID 18670389HCID 18670389, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

200 mg of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]-benzothiazin-8-ylmethyl)acetonitrile was dissolved in 5 ml of dimethyl sulfoxide. After adding 200 mg of powdered potassium hydroxide, the resulting mixture was heated to 40 to 60° C. for 10 minutes. Then the reaction mixture was distributed into 1 N hydrochloric acid and ethyl acetate. The organic layer was extracted, washed successively with a saturated aqueous solution of sodium bicarbonate and water and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 35 mg of the title compound as yellow crystals.

Workup

  1. extractionThe organic layer was extracted
  2. washwashed successively with a saturated aqueous solution of sodium bicarbonate and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-c2163aa7b9914118b6de26d48bb5408a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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