Triazine compound as well as preparation method and application thereof
A compound and triazine technology, applied in the field of preparation of triazine compounds, can solve the problems of single structure, the lack of non-covalent high-efficiency 3CLpro small molecule inhibitors, etc., and achieve small toxic side effects, good inhibitory activity, good effect of treatment
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Embodiment 1
[0069] Example 1 Synthesis of compound IV-1
[0070]
[0071] Step 1: Synthesis of Compound 2
[0072] To a solution of compound 2 (100.0 mg, 0.47 mmol) in N,N-dimethylformamide (10 mL), potassium hydroxide (105.5 mg, 1.88 mmol) and iodine (239 mg, 0.94 mmol) were added, and the reaction was carried out at room temperature. After 3 hours, TLC monitored the completion of the reaction. Saturated sodium sulfite solution was added to quench the reaction. The aqueous phase was extracted with ethyl acetate (10 mL*2), washed with water (20 mL*2), and washed with saturated salt (20 mL) with anhydrous sodium sulfate. Dry and concentrate by column chromatography to obtain compound 3 (134.8 mg, 85%). 1 HNMR (300 MHz, CDCl 3 ) δ 8.79 (s, 1H), 7.70 (s, 1H), 3.90 (s, 3H).
[0073] Step 2: Synthesis of Compound 3
[0074] To a solution of compound 3 (120.0 mg, 0.36 mmol) in deuterated acetic acid (8 mL), sodium acetate (97.9 mg, 0.72 mmol) was added, the dropwise addition was complete...
Embodiment 2
[0077] Example 2 Synthesis of compound IV-2
[0078]
[0079] To compound 4 (30 mg, 0.17 mmol) was added deuterated acetic acid (2 mL), refluxed at 120 °C for 25 hours, TLC monitored the completion of the reaction, and concentrated under reduced pressure to obtain compound IV-2 (28 mg, 92%). 1 H NMR (300 MHz, CDCl 3 ) δ 7.44(s, 1H), 5.11 (d, J = 7.1 Hz, 1H), 4.95 (d, J = 7.1 Hz, 1H), 3.85 (s, 3H).
Embodiment 3
[0080] Example 3: Synthesis of Compound S1
[0081]
[0082] Step 1: Synthesis of Compound 6
[0083] Compound 5 (18 g, 78.8 mmol) was dissolved in acetonitrile (240 mL), to the above solution was added compound 11 (26 g, 118.8 mmol) and K 2 CO 3 (16.4 g, 118.8 mol), the reaction solution was heated to reflux for 3 h. The reaction solution was cooled to room temperature, filtered with suction, the filtrate was concentrated, and separated and purified by column chromatography (PE:EA=30:1) to obtain compound 6 (23.5 g, 80%). 1 H NMR (300 MHz, CDCl 3 ) δ 1.33 (3H, t, J = 7.4 Hz), 1.65 (9H, s), 3.15 (2H, q, J =7.4 Hz), 5.03 (2H, s), 6.91−7.01 (2H, m).
[0084] Step 2: Synthesis of Compound 7
[0085] Compound 6 (20 g, 51.9 mmol) was dissolved in TFA (39 mL), the reaction was stirred at room temperature for 6 h, the stirring was stopped, the TFA was evaporated under reduced pressure, slurried with ether, filtered with suction, the filter cake was collected, and dried in vac...
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