Ethyl Acetate → HCID 18670663, compound

HRID 1059308Notes

Reaction equation

HRID 1059308 reaction equation
[NH2:1][C:2]1[C:3]([SH:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].Cl[C:16]1[C:21](Cl)=[N:20][CH:19]=[CH:18][N:17]=1.C(OCC)(=O)C>CN(C)C=O>[N:17]1[C:18]2[NH:1][C:2]3[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[N:4][C:3]=3[S:12][C:19]=2[N:20]=[CH:21][CH:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 785752,3-DichloropyrazineHCID 178498866HCID 178498866, compound

Product 1

HCID 18670663HCID 18670663, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of methyl 5-amino-6-mercaptonicotinate in N,N-dimethylformamide (30 ml) were added 0.52 g of sodium hydride (oily: 60% or more) and 0.97 g of 2,3-dichloropyrazine and the resulting mixture was reacted at 100° C. for 2 hours. Then ethyl acetate was added to the reaction mixture, which was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, diethyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 0.43 g of crude methyl 10H-pyrazino[2,3-b]pyrido[3,2-e][1,4]thiazin-8-carboxylate as a brown solid. To a solution of 1.43 g of these crude crystals in N,N-dimethylformamide (50 ml) were added 0.26 g of sodium hydride (60% oily) and 0.5 g of chloromethyl methyl ether and the resulting mixture was reacted under ice-cooling for 1 hour. After adding ethyl acetate, the mixture was washed with a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, diethyl ether was added to the residue and the crystals thus precipitated were taken up by filtration to thereby give 1.5 g of the title compound as red crystals.

Workup

  1. customthe resulting mixture was reacted at 100° C. for 2 hours
  2. washwas then 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, diethyl ether
  5. additionwas added to the residue
  6. customthe crystals thus precipitated
  7. filtrationwere taken up by filtration

Sources & evidence

ORD record
ord-c6a5b47fb21848ddace79acc5e6227c2
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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