Water → HCID 18670694, compound

HRID 1059404Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[CH3:8][O:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([CH2:21]Cl)[CH:19]=[CH:20][C:15]=2[S:14][C:13]2[N:23]=[CH:24][CH:25]=[N:26][C:12]1=2.O>CN(C)C=O.C(OCC)(=O)C>[CH3:8][O:9][CH2:10][N:11]1[C:16]2[CH:17]=[C:18]([CH2:21][N:1]3[CH:5]=[CH:4][CH:3]=[N:2]3)[CH:19]=[CH:20][C:15]=2[S:14][C:13]2[N:23]=[CH:24][CH:25]=[N:26][C:12]1=2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 100 mg of pyrazole in N,N-dimethylformamide was added in a nitrogen atmosphere 60 mg of sodium hydride (oily 60%) under ice cooling and the resulting mixture was stirred for 10 minutes. Subsequently, 240 mg of 10-methoxymethyl-8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine was added to the reaction mixture, which was then heated to 80° C. for 10 minutes. Then the reaction mixture was brought back to room temperature and distributed into water and ethyl acetate. The organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue thus obtained was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 150 mg of the title compound as a yellow powder.

Workup

customwas brought back to room temperature
extractionThe organic layer was extracted
washwashed with water
dry with materialdried over anhydrous sodium sulfate
distillationAfter distilling off the solvent under reduced pressure
customthe residue thus obtained
customwas purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record: ord-d67f6ef28cff401faad2e938db298d6e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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