With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.87988-94-1,5-Methylisoxazol-4-amine,as a common compound, the synthetic route is as follows.,87988-94-1
Example 8(a) 5-Acetyl-l-(tetrahydro-2H-pyran-4-yl)- 2-trifluoromethyl-lH-imidazole; 5-Methyl-4-amino-isoxazole (1.7 g, 17.25 mmol) and acetic acid (1.1 g, 19 mmol) were dissolved in methanol (50 mL). Tetrahydro-2H-pyran-4-one (1.9 g, 19 mmol) was added and the mixture was cooled to 0 – (-5) 0C and stirred for 1 h. Sodium cyanoborohydride (0.812 g, 12.9 mmol) was added in portions to the reaction mixture at -5 C, causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 2 h followed by addition of water (20 mL). The methanol was removed from the reaction mixture, and the intermediate amine was extracted with ethyl acetate (3×80 mL). The combined organic layers were dried (Na2SO4), concentrated to dryness, dissolved in toluene and re-concentrated. The crude intermediate amine, was dissolved in CH2Cl2 (20 mL) and pyridine (2 mL, 26 mmol) was added. The mixture was cooled to 0C and trifluoroacetic anhydride (4.35 g, 20.7 mmol) was added dropwise. The mixture was continued stirring for 2 h at r.t. and was then washed with water and saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 (2×30 mL), the organic extracts were dried (Na2SO4) and concentrated to dryness to give a second crude intermediate, 4-[N- (tetrahydro-2H-pyran-4-yl)]-N-trifluoroacetyl-amino-5-methylisoxazole. MS (ES) m/z 279 (M++.). The title compound was prepared in accordance with the general method of Example 6 (b) using the intermediate 4-[N-(tetrahydro-2H-pyran-4-yl)]-N-trifluoroacetyl- amino-5-methylisoxazole (max 17.25 mmol), with the exception that the product was purified by flash chromatography (heptane/EtOAc 3:2), giving the title compound (3.03 g, 67%).1H nuMR (CDCl3, 300 MHz) delta 7.85 (s, 1 H), 4.89-4.75 (m, 1 H), 4.17-4.07 (m, 2 H), 3.54- 3.44 (m, 2 H), 2.75-2.60 (m, 2 H), 2.56 (s, 3 H), 1.72-1.63 (m, 2 H); MS (ES) m/z 263 (M+l).
87988-94-1 5-Methylisoxazol-4-amine 13033202, aIsoxazoles compound, is more and more widely used in various fields.
Reference£º
Patent; ASTRAZENECA AB; WO2008/2244; (2008); A2;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem