反应详情

温度

65 °C

2-(4-(4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-ylamino)ethyl methanesulfonate (50.0 g, 0.108 mol) was dissolved in N,N-dimethylformamide (83 mL). Sodium azide (10.5 g, 0.162 mol) was added. The reaction was stirred at 65° C. for 5-6 hours. LCMS indicated reaction completed (M+Na=435). The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2×250 mL). The combined ethyl acetate solution was washed with water (250 mL, layer separation was slow, 100 mL of brine was added to improve the separation), dried over sodium sulfate, and concentrated to give 49.7 g crude brown solid. Crude yield is 112%. LCMS for C12H8BrFN8O3Na (M+Na)+: m/z=433.0, 435.0. 1H NMR (400 MHz, DMSO-d6): δ 8.08 (dd, J=6.2, 2.5 Hz, 1 H), 7.72 (m, 1 H), 7.58 (t, J=8.7 Hz, 1 H), 6.75 (t, J=5.7 Hz, 1 H), 3.54 (t, J=5.3 Hz, 2 H), 3.45 (dd, J=11.1, 5.2 Hz, 2 H).

1. customreaction
2. customThe reaction was quenched with water (250 mL)
3. extractionextracted with ethyl acetate (2×250 mL)
4. washThe combined ethyl acetate solution was washed with water (
5. custom250 mL, layer separation
6. addition100 mL of brine was added
7. customthe separation),
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated