Reference of 53135-24-3 ,Some common heterocyclic compound, 53135-24-3, molecular formula is C8H10N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
General procedure: Compound 17 c (2.90 g, 21 mmol) and diethyl (ethoxymethylidene)propanedioate (4.25 mL, 21 mmol) were dissolved in EtOH (30 mL). A solution of sodium ethoxide (20% in EtOH; 14.3 g, 42 mmol) was added to the solution dropwise at 0 C. After stirring at 80 C for 15 h, the reaction mixture was concentrated in vacuo. The residue was acidified with 1M HCl to pH 3. The precipitate was collected by filtration and washed with small amount of water. The product obtained (2.90 g, 13 mmol) was dissolved in POCl3 (9.6 g). After stirring at 100 C for 2 h, the reaction mixture was concentrated in vacuo. The residue was cooled to 0 C, neutralized with a saturated aqueous NaHCO3 solution to pH 7, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. A solution of the product obtained, furfurylamine (1.20 mL, 12.9 mmol), and diisopropylethylamine (2.26 mL, 12.9 mmol) in 2-propanol (10 mL) was stirred under reflux for 15 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with a saturated aqueous NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc=9:1 to 5:1). The product obtained was dissolved in 2M NaOH (15mL, 30mmol), EtOH (15mL), and THF (5mL). After stirring at room temperature for 15h, the mixture was acidified with 1M HCl to pH 3.0. The precipitate was collected by filtration and washed with water to give 18c as a colorless powder (3.30g, 57%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53135-24-3, its application will become more common.
Reference:
Article; Imaeda, Yasuhiro; Tawada, Michiko; Suzuki, Shinkichi; Tomimoto, Masaki; Kondo, Mitsuyo; Tarui, Naoki; Sanada, Tsukasa; Kanagawa, Ray; Snell, Gyorgy; Behnke, Craig A.; Kubo, Keiji; Kuroita, Takanobu; Bioorganic and Medicinal Chemistry; vol. 24; 22; (2016); p. 5771 – 5780;,
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