1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 25234167, compound

Participants

Reaction Steps

To a solution of N′-acetyl-4-(1-methyl-1H-imidazol-4-ylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carbohydrazide (25 mg, 63 μmol) in THF (1 mL) was added DBU (14 mg, 95 μmol) and Burgess reagent (75 mg, 316 μmol). The reaction vial was capped subjected to microwave irradiation (150° C., 10 min). LCMS analysis of the reaction mixture indicated that the starting material had been consumed. The reaction was diluted with saturated aqueous NaHCO3 (1 mL) and EtOAc (2 mL). The organic layer was removed and the aqueous layer was extracted with EtOAc (2 mL). The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography with a gradient elution of hexanes with 10-60% EtOAc to provide 2-methyl-5-(4-(1-methyl-1H-imidazol-4-ylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)-1,3,4-oxadiazole (16 mg, 42 μmol, 67% yield). LCMS (+ESI) m/z=377.8 [M+H]+; 1H-NMR (CDCl3) δ 8.05 (m, 2H), 7.9 (d, 2H), 7.8 (d, 2H), 7.4-7.5 (m, 3H), 7.25 (d, 1H), 7.1 (dd, 1H), 6.75 (d, 1H), 3.5 (t, 2H), 3.1 (t, 2H).

Provenance & Evidence