Hydrazine hydrate (1:1) → 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

HRID 1059427Notes

Reaction equation

[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][N:15]3C(=O)C4=CC=CC=C4C3=O)[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:26]=[CH:27][CH:28]=[N:29][C:5]1=2.O.NN>C(O)C>[NH2:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]2[S:7][C:6]3[N:26]=[CH:27][CH:28]=[N:29][C:5]=3[N:4]([CH2:3][O:2][CH3:1])[C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.3 g of N-(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)phthalimide in 20 ml of ethanol was added 5 ml of hydrazine monohydrate and the resulting mixture was heated to 60° C. for 10 minutes. After distilling off the solvent under reduced pressure, the residue was distributed into a 5% aqueous solution of sodium hydroxide and ethyl acetate. The organic layer was extracted and the extract was dried over potassium carbonate. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia) to thereby give 890 mg of the title compound as a yellow oily substance.

Workup

distillationAfter distilling off the solvent under reduced pressure
extractionThe organic layer was extracted
dry with materialthe extract was dried over potassium carbonate
distillationAfter distilling off the solvent under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record: ord-4bbd95010bb649d5ac95b904b52fb8be
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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