Water → Ethyl [3-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-3-azabicyclo[3.1.0]hex-6-yl]carboxylate

HRID 1059370Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][NH:9][CH2:10]2)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].Cl[CH2:18][C:19]1[CH:20]=[CH:21][C:22]2[S:27][C:26]3[N:28]=[CH:29][CH:30]=[N:31][C:25]=3[NH:24][C:23]=2[CH:32]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][N:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]3[S:27][C:26]4[N:28]=[CH:29][CH:30]=[N:31][C:25]=4[NH:24][C:23]=3[CH:32]=1)[CH2:10]2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.523 g of ethyl(3-azabicyclo[3.1.0]hex-6-yl)carboxylate in N,N-dimethylformamide (30 ml) were added 2.30 g of sodium hydrogencarbonate and 1.39 g of 8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and the resulting mixture was heated to 80° C. for 2 hours. After adding water and ethyl acetate, the organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Then the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.574 g of the title compound as pale yellow crystals.

Workup

washthe organic layer was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThen the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record: ord-ed445e65dc544faf96eefe21a7be4870
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518423B1

Reaction notes

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