反应详情

温度

75 °C

N-(7-Oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (Stage T.4, 2.286 g, 10.87 mmol) was dissolved in AcOH (60 ml), then bromine (1.74 g, 10.87 mmol) dissolved in AcOH (10 mL) were slowly added and the RM was heated to 75° C. for 20 h. The color changed from red to beige. The mixture was evaporated and the residue was dissolved in MeOH (10 mL) and precipitated with H2O. The mixture was filtered and dried on HV. The crude material was chromatographed with MPLC C18 H2O 0.1% TFA/CH3CN 0.1% TFA, gradient 0-50%. Fractions containing the product were neutralized with NaHCO3, extracted with EtOAc and lyophilized from dioxane to give of the title compound as a white solid (M+H=291; M−H=289; tR 4.29 (Method F)). 1H-NMR (d6-DMSO, 600.13 MHz) 12.75 (s, 1H) 4.95 (t, 1H), 2.95-2.84 (m, 2H), 2.62-2.52 (m, 1H), 2.40-2.30 (m, 1H), 2.20 (s, 3H).

1. additionwere slowly added
2. customThe mixture was evaporated
3. dissolutionthe residue was dissolved in MeOH (10 mL)
4. customprecipitated with H2O
5. filtrationThe mixture was filtered
6. customdried on HV
7. customThe crude material was chromatographed with MPLC
8. additionFractions containing the product
9. extractionextracted with EtOAc