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

HRID 748176Notes

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.[CH:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.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:26]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(6-methylamino-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.20 g, 0.72 mmol), cyclohexanecarbonyl chloride (0.22 g, 1.5 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 successively washed 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 tetrahydrofuran-hexane to give the titled compound (0.20 g, 71%).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washThe extract was successively washed 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 tetrahydrofuran-hexane

Sources & evidence

ORD record: ord-645495ed392c476f98454559d9ae7cd9
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399759B2

Reaction notes

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