Supplementary Materialsmolecules-22-01925-s001. on silica gel (petroleum ether:ethyl acetate = 4:1) to give 7 (0.39 g, 62.9%) as a white solid. (13a). Intermediate 7 (0.20 g, 1 mmol) was dissolved in acetonitrile (10 mL), and phosphorus oxychloride (0.17 mL, 1.9 mmol) was added in a slow stream. The perfect solution is was heated at reflux for 4 h and cooled to room temperature and concentrated then. Ethyl acetate (20 mL) was added, cleaned with brine and drinking water, dried out over Na2SO4, and focused in vacuo. The residue was purified by chromatography on silica gel (petroleum ether:ethyl acetate = 20:1) to provide 13a (0.13 g, 66.2%) like a white colored stable. (13b). Intermediate 7 (0.30 g, 1.4 mmol) was dissolved in tetrahydrofuran (5 mL), and Lawessons reagent (0.34 g, 0.80 mmol) was added. The perfect solution is was heated at reflux for 4 h and cooled to room temperature then. The solvent was eliminated under decreased pressure, as well as the ensuing residue was dissolved in ethyl acetate. The perfect solution is was cleaned with brine and drinking water, dried out over Na2SO4, and focused in vacuo. The residue was purified by chromatography on silica gel (petroleum ether:ethyl acetate = 10:1) to provide 13b (0.10 g, 59.6%) like a white stable. (9). Phenylhydrazine (0.50 g, 5.0 mmol) and ethyl acetopyruvate (1.1 g, 7.0 mmol) were dissolved in ethanol (10 Rabbit Polyclonal to SLC6A6 mL). After becoming warmed at reflux for 2 h, the response blend was cooled to space temperature and focused in vacuo. The residue was dissolved in ethyl acetate, cleaned with drinking water and brine, dried out over Na2SO4, and focused in vacuo. The residue was purified by chromatography on silica gel (petroleum ether:ethyl acetate = 10:1) to provide 9 (0.50 g, 43.6%) like a white stable. (13c). In a remedy of intermediate 9 (92.1 mg, 0.40 mmol) dissolved in ethanol (5 mL), sodium borohydride (19.0 mg, 0.50 mmol) was added. The blend LP-533401 supplier was stirred at space temp for 30 min, and drinking water was added. The perfect solution is was extracted with ethyl acetate, as well as the mixed organic levels had been cleaned with brine and drinking water, dried out over Na2SO4, and focused in vacuo. The residue was dissolved in DMF (2 mL); after that thionyl chloride (0.10 mL, 1.4 mmol) was added. After reflux for 1 h, drinking water was extracted and added with ethyl acetate. The mixed organic levels had been cleaned with brine and drinking water, dried out over Na2SO4, and focused in vacuo. The residue was purified by chromatography on silica gel (petroleum ether:ethyl acetate = 10:1) to provide 13c (66.6 mg, 80.5%) like a white stable. (11). An assortment of 2-bromo-1-phenylethan-1-1 (0.50 g, LP-533401 supplier 2.5 mmol) and ethyl 2-amino-2-thioxoacetate (0.50 g, 3.8 mmol) was dissolved in ethanol (10 mL). The perfect solution is was warmed at reflux for 6 h and cooled to room temperature. After being concentrated, the residue was dissolved in ethyl acetate (20 mL); then the solution was washed with LP-533401 supplier water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether:ethyl acetate = 20:1) to give 11 (0.43 g, 73.6%) as a white solid. (13d). The ester function in 11 was reduced with NaBH4 and reacted subsequently with SOCl2 to afford 13d, and this operation was the same as the step in the synthetic intermediate 13c. Compound 13d was obtained as LP-533401 supplier a white solid. Yield: 75.9%. (13e). A mixture of benzohydrazide (0.50 g, 3.7 mmol), 2-chloroacetic acid (0.35 g, 3.7 mmol), and phosphorus oxychloride (1.0 mL, 11.0 mmol) was added to a three-necked round bottom flask. The solution was heated at reflux for 6 h and then cooled to 0 C and neutralized to pH 9 with a saturated sodium carbonate aqueous solution. The precipitate was filtered, washed with water, and dried under an infrared lamp. Compound 13e (0.58 g, 81.1%) was obtained as a white solid. (13f). A mixture of benzene-1,2-diamine (2.0 g, 18.0 mmol) and ethyl 2-chloroacetate, (2.6 mL, 24.0 mmol) was dissolved in dilute hydrochloric acid solution (4 mol/L, 16 mL). The solution was heated at 110 C LP-533401 supplier for 4 h and then cooled to room temperature. The reaction solution was poured into ice water and then neutralized to pH 9 with ammonium hydroxide. The precipitate was filtered, washed with water, and dried under an infrared lamp to obtain compound 13f (2.7 g, 91.3%) was obtained as a white.