3-oxide-2-methylamide derivatives as well as preparation method and use thereof
A technology of oxypyrazine and formamide, which is applied in the field of pyrazine-2-carboxamide derivatives, can solve the problems of low water solubility, achieve the effects of improved solubility, improved antiviral activity, and high yield of finished products
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[0029] Synthesis Example One
[0030] Synthesis of compound 9:
[0031] Dissolve compound 7 (1.72 g, 0.01 mol) in 30 ml of DMF, add K 2 CO 3 (3g), 2-chloromethoxyethyl acetate 8 (1.53g, 0.01mol). A trace of KI was added to the mixture, and stirred at room temperature for 12 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in 100 ml of chloroform. It was washed once with water, washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (using 10% methanol-dichloromethane) to obtain compound 9 (1.95 g, yield 68%). Melting point 188-190°C. HRMS(ESI)Calcd.for C 11 H 13 FN 2 O 6 : 288.2292; Found 288.2290.
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[0032] Synthesis Example 2
[0033] Synthesis of compound 2:
[0034] Compound 9 (1 g, 0.0035 mol) and 7N ammonia methanol solution were mixed at room temperature and sealed for three days. The solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (10% methanol-dichloromethane). Compound 2 (0.75 g, 93%). Melting point 212-215°C. HRMS(ESI)Calcd.for C 8 H 10 FN 3 O 4 : 231.1812; Found 231.1810.
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[0035] Synthesis Example Three
[0036] Synthesis of compound 10:
[0037] Compound 2 (2.31 g, 0.01 mol) was dissolved in 70 ml of dry dichloromethane, and tetra-tert-butoxy (0.4 mL, 0.01 mol), triethylamine (2.12 mL, 0.015 mol) and diethyl chlorophosphate were added (1.42mL, 0.01mol). The mixture was stirred at room temperature for 24 hours, 80 mL of water was added, the organic layer was separated, and the aqueous phase was extracted with ethyl acetate (3×100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated in vacuo, and the residue was chromatographed on a silica gel column. Separate (using 5% methanol-dichloromethane) to obtain compound 10 (3.2 g, yield 87%). HRMS(ESI)Calcd.for C 12 H 19 FN 3 O 7 P: 368.2674; Found 368.2675.
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