Pyridine → 8-Chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

HRID 1059273Notes

Reaction equation

HRID 1059273 reaction equation
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15]O)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.CS([Cl:27])(=O)=O.C(Cl)Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:27][CH2:15][C:12]1[CH:13]=[CH:14][C:7]2[S:6][C:5]3[N:4]=[CH:3][CH:2]=[N:1][C:10]=3[NH:9][C:8]=2[CH:11]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1094429210H-Pyrazino[2,3-b][1,4]benzothiazine-8-methanolHCID 23716255Sodium bicarbonate methylene chloride

Product 1

HCID 117470388-Chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of 7 g of 10H-pyrazino[2,3-b][1,4]benzothiazine-8-methanol and 6.1 ml of pyridine in N,N-dimethylformamide (50 ml) was added dropwise 5.9 ml of methanesulfonyl chloride at 0° C. After stirring at room temperature for 1 hour, the reaction mixture was poured into a pre-cooled aqueous solution of methylene chloride/sodium hydrogencarbonate, extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crystals thus precipitated were diluted with a small amount of ethyl acetate, taken up by filtration and washed with diethyl ether. Thus 4.7 g of the title compound was obtained as a yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe crystals thus precipitated
  6. additionwere diluted with a small amount of ethyl acetate
  7. filtrationtaken up by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-acf4eca3cbe3444dbf31cd03ab5bdd33
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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