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Stage #1: salirasib With 1,1'-carbonyldiimidazole In tetrahydrofuran at 30 - 40℃; for 2h;
Stage #2: 4-(diethylamino)butylamine In tetrahydrofuran at 20℃;
3 Synthesis of compound 5:
a mixture of compound (m) (3.59 g, 11.0 mmol) and CDI (2.33 g, 14.3 mmol, 1.30 eq.) in THF (40.0 mL) was stirred at 30-40 °C for 2 h. Compound (m) (2.38 g, 16.5 mmol, 1.5 eq.) in THF (15 mL) was added to the mixture at room temperature slowly. The resulting mixture was stirred at room temperature overnight togive a clear yellowish solution. After the reaction was complete as monitored by HPLC, solvent was evaporated under reduced pressure. Then DCM (100 mL) and H20 (30.0 mL) were added to the reaction mixture. The aqueous layer was extracted with DCM (40.0 mL x 3). The combined organic layer was washed with H20 (40.0 mL x 3), brine (30.0 mL), dried over Mg504, evaporated and purified by flash chromatography (0% -15% MeOHIDCM) toafford compound 5 (4.95 g) in 92.7% yield.