HCID 18670265, compound → (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)methyl ketone

HRID 1059373Notes

Reaction equation

HRID 1059373 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:16]=[CH:17][CH:18]=[N:19][C:5]1=2.[CH3:20][Li]>O1CCCC1.C(OCC)C.ClCCl.[O-2].[O-2].[Mn+4]>[CH3:20][C:14]([C:11]1[CH:12]=[CH:13][C:8]2[S:7][C:6]3[N:16]=[CH:17][CH:18]=[N:19][C:5]=3[N:4]([CH2:3][O:2][CH3:1])[C:9]=2[CH:10]=1)=[O:15]

Participants

7

Reactant 2

HCID 18670265HCID 18670265, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18670297(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)methyl ketone

Reagents, catalysts & solvents 4

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 16 g of 10-(methoxymethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine-8-carboxaldehyde in 200 ml of tetrahydrofuran was dropped at −78° C. 60 ml of a 1.4 M solution of methyllithium in diethyl ether. Next, the resulting mixture was heated to room temperature over 2 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 16 g of a yellow oily substance was obtained. To a solution of 16 g of this oily substance in dichloromethane (300 ml) was added 100 g of manganese dioxide and the resulting mixture was stirred at room temperature for 17 hours. After the completion of the reaction, the manganese dioxide was filtered off. The filtrate was concentrated and the residue thus obtained was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 9. 4 g of the title compound. as yellow. crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure, 16 g of a yellow oily substance
  5. customwas obtained
  6. customAfter the completion of the reaction
  7. filtrationthe manganese dioxide was filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe residue thus obtained
  10. customwas purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
  11. customto thereby give 9

Sources & evidence

ORD record
ord-5a4779689e5146898729f5bd45e6c96a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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