Nitrogen-containing bicyclic compound, preparation method and uses thereof
A technology for compounds and heterobicycles, which can be applied in the directions of active ingredients of heterocyclic compounds, preparation of sugar derivatives, chemical instruments and methods, etc., and can solve problems such as drug resistance and transformation.
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Embodiment 1
[0171] Example 1. 3-methoxy-1-pentyl-4-(2-pyridyl)-1,6-naphthyridine-2 (1 H )-ketone
[0172]
[0173] Step 1) Under nitrogen protection, 3-(4-aminopyridine)-2-pyridinemethanone (2 mmol), methoxyacetyl chloride (3.8 mmol) and N, N-diisopropylethylamine (8 mmol) was dissolved in dichloromethane (5 mL) and reacted at room temperature for 3 hours. After pointing the plate, it was found that the reaction of the raw materials was complete. The reaction solution was diluted with water and extracted with ethyl acetate. After the organic phase was decompressed to remove the solvent, the residue was purified by silica gel column chromatography to obtain 3-(4-methoxyacetamido)-2-pyridine ketone.
[0174] Step 2) Under nitrogen protection, 3-(4-methoxyacetamido)-2-pyridinemethanone (1.0 mmol) was dissolved in tetrahydrofuran (10 mL), and t-BuOK (10 mmol) was added to react at room temperature 5 Hour. The reaction solution was extracted with saturated ammonium chloride solution and...
Embodiment 2
[0178] Example 2. 1-cyclopentyl-3-methoxy-4-(4-methoxyphenyl)-7-propionyl-1,6-naphthyridine-2(1 H )-ketone
[0179]
[0180] Step 1) Under nitrogen protection, 1-(4-amino-5-(4-methoxybenzoyl)-pyridin-2-propyl-1-one (2 mmol), methoxyacetyl chloride ( 3.8 mmol) and N,N-diisopropylethylamine (8 mmol) were dissolved in dichloromethane (5mL), and reacted at room temperature for 3 hours. The reaction of the raw materials was found to be complete by spotting the plate, and the reaction solution was diluted with water and extracted with ethyl acetate. After removing the solvent from the organic phase under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1-(4-methoxyacetamido-5-(4-methoxybenzoyl)-pyridine-2-propyl-1- ketone.
[0181] Step 2) Under nitrogen protection, 1-(4-methoxyacetamido-5-(4-methoxybenzoyl)-pyridin-2-propyl-1-one (1.0 mmol) was dissolved in THF ( 10 mL), added t-BuOK (10 mmol) and reacted at room temperature for 5 hours...
Embodiment 3
[0185] Example 3. N,N-dimethylglycine-3-(3-methoxy 4-(3-methoxyphenyl)-2-oxoquinoline-1(2 H )-yl)propyl ester
[0186]
[0187] Step 1) 3-methoxy-4-(3-methoxyphenyl)quinoline-2(1 H The synthetic method of )-ketone is with reference to embodiment 1 and 2.
[0188] Step 2) Under nitrogen protection, CuI (1 mmol), Cs 2 CO 3 (20 mmol) and ethyl 2-oxocyclohexylcarboxylate (2 mmol) were added into DMSO (10 mL), and stirred at room temperature for 30 min. 3-methoxy-4-(3-methoxyphenyl)quinoline-2(1 H )-ketone (10 mmol) and 3-bromo-N,N-dimethylglycine propyl ester (10 mmol) in DMSO (12 mL) were added by injection. Heat to 100°C overnight. Cool to room temperature, filter, add water (50 mL) and dichloromethane (50 mL×3), collect the organic phase, evaporate the solvent under reduced pressure, and purify the crude product by column chromatography to obtain N,N-dimethylglycine- 3-(3-methoxy 4-(3-methoxyphenyl)-2-oxoquinoline-1(2 H )-yl)propyl ester.
[0189] ESI-MS (m / z): 425....
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