反应详情

温度

65 °C

Sodium azide (20.45 mg, 0.315 mmol, 3.0 equiv) was added to a stirring solution of the product of Step 1 (53 mg, 0.11 mmol) in chloroform (5 ml). Methanesulfonic Acid (0.082 ml, 1.258 mmol, 12 equiv) was added and the reaction was capped and stirred at 65° C. for 1 h. The yellow mixture was partitioned between EtOAc (2×85 ml) and saturated aqueous NaHCO3 (90 ml), and the combined organic layers were dried over MgSO4 and concentrated. The residual colorless oil was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present). The desired fractions were partitioned between EtOAc (2×55 ml) and saturated aqueous NaHCO3 (65 ml). The combined organic layers were dried over Na2SO4 and concentrated, providing the desired title compound (1.3 mg, 2.5%) as a colorless solid-oil. MS ESI: [M+H]+ m/z 477.21. 1H NMR (500 MHz, CD3OD) δ 8.72 (d, 1H, J=4.6 Hz), 8.19 (bs, 1H), 7.98 (s, 1H), 7.44 (s, 1H), 7.16 (s, 1H), 7.13 (d, 1H, J=4.6 Hz), 3.45 (s, 2H), 2.95 (m, 2H), 2.05 (s, 3H), 1.90-1.57 (m, 6H). rhSYK activity=+++

1. customthe reaction was capped
2. customThe yellow mixture was partitioned between EtOAc (2×85 ml) and saturated aqueous NaHCO3 (90 ml)
3. dry with materialthe combined organic layers were dried over MgSO4
4. concentrationconcentrated
5. customThe residual colorless oil was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)
6. customThe desired fractions were partitioned between EtOAc (2×55 ml) and saturated aqueous NaHCO3 (65 ml)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. concentrationconcentrated