Dimethylacetamide → N-Methyl-N-[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]-2-furamide

HRID 748173Notes

Reaction equation

[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH:6]=[CH:5][CH:4]=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](Cl)=[O:26].CN(C)C(=O)C>O>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[N:8]=1)[C:25]([C:21]1[O:20][CH:24]=[CH:23][CH:22]=1)=[O:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(6-methylamino-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.20 g, 0.74 mmol), 2-furoyl chloride (0.26 g, 2.0 mmol) and N,N-dimethylacetamide (10 ml) was stirred at 80° C. for 2 hrs. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine and dried. The solvent was evaporated. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (1:1, v/v). The obtained crystals were recrystallized from ethyl acetate-hexane to give the titled compound (0.21 g, 63%)

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
customdried
customThe solvent was evaporated
washeluted with hexane-ethyl acetate (1:1
customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-5252f74d8164491a89364dfa3a7f7646
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399759B2

Reaction notes

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