The synthetic route of 87988-94-1 has been constantly updated, and we look forward to future research findings.
87988-94-1, 5-Methylisoxazol-4-amine is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,87988-94-1
Example 7 fa) 4-[N-Acetyl-N-(tetrahydro-2H-pyran-4-yl)]amino-5-methylisoxazole; 5-Methyl-4-amino-isoxazole (Reiter, L.A., J. Org. Chem. 1987, 52, 2714-2726) (0.68 g, 5.1 mmol) and acetic acid (0.61 g, 10.2 mmol) were dissolved in MeOH (20 mL). Tetrahydro-2H-pyran-4-one (0.76 g, 7.6 mmol) was added and the mixture was cooled to 0 – (-5) 0C and stirred for 1 h. Sodium cyanoborohydride (0.32 g, 5.1 mmol) was added to the reaction mixture at -5 0C, causing weak exothermic and gas evolution. The cooling bath was removed and the mixture was stirred at r.t. for 1 h, followed by the addition of a second portion of sodium cyanoborohydride (0.1 g, 1.6 mmol). After stirring for 2 h at r.t, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in toluene and re-concentrated. The residue was dissolved in THF (10 mL) and acetic anhydride (1.56 g, 15.3 mmol) was added. The resulting mixture was stirred overnight at r.t. then for 1 h at +50 C. The volatiles were removed in vacuo and the residue was dissolved in toluene and concentrated in vacuo to give the title compound (1.36 g, 78%).1H NMR (CDCl3) ppm delta 8.04 (s, 1 H), 4.86-4.73 (m, 1 H), 4.00-3.89 (m, 2 H), 3.52-3.42 (m, 2 H), 2.35 (s, 3 H), 1.81 (s, 3 H), 1.70-1.57 (m, 2 H), 1.49-1.23 (m, 2 H); MS (ESI) m/z 225 (M+l).; Example 9(a) 5-Acetyl-l-(tetrahydro-2H-pyran-4-yl)- 2-trtfluoromethyl-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) C 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 by vacuum distillation, 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- [iV-(tetrahydro-2H-pyran-4-yl)]-iV-trifluoroacetyl-amino-5-methylisoxazole. MS (ES) m/z 279 (M++l). 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,1H NMR (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).
The synthetic route of 87988-94-1 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ASTRAZENECA AB; WO2008/2245; (2008); A2;,
Isoxazole – Wikipedia
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