Benzopyridine azepines and their applications
A kind of technology of benzopyridine azepine and benzopyridine, which is applied to the application field in the preparation of antitumor compounds
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Embodiment 1
[0090] Synthesis of N-benzyl-4-chloro-3-nitro-N-phenylpyridin-2-amine (intermediate 3-1)
[0091] Take 2,4-dichloro-3-nitropyridine (1.93g, 10mmol) and K 2 CO 3 (1.66g, 12mmol) was dissolved in DMF 10mL, and N-benzylaniline (1.83g, 10mmol) in DMF solution 10mL was slowly added dropwise thereto, and the reaction was stirred at room temperature for 12h. After the reaction, 30 mL of ethyl acetate was added to dilute, washed with water (20 mL×3), diluted hydrochloric acid (1M, 10 mL), and saturated brine (20 mL), and the organic layer was dried over anhydrous sodium sulfate. After filtration and concentration, the resulting solid was recrystallized from ethanol to obtain 2.91 g of a yellow solid, with a yield of 85.6%.
[0092] ESI-MS[M+H] + :m / z 340.3
[0093] 1 H NMR (400MHz, DMSO-d 6)δppm: 8.40(d,1H,J=7Hz,pyridine-6-H),6.87~7.84(m,11H,Ar-H,pyridine-5-H),4.53(s,2H,CH 2 ).
Embodiment 2
[0095] N 2 -Benzyl-4-chloro-N 2 -Synthesis of phenylpyridine-2,3-diamine (intermediate 4-1)
[0096] Take intermediate 3-1 (3.40g, 10mmol) and dissolve it in a mixed solution of ethanol 40mL and water 10mL, add iron powder (1.68g, 30mmol) and NH 4 Cl (0.32g, 6mmol). The temperature was raised to reflux, and the reaction was stirred for 5h. After the reaction, cool to room temperature, filter through diatomaceous earth, concentrate the filtrate, add 50 mL of ethyl acetate to dilute, and wash with saturated NaHCO 3 solution, water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by silica gel column chromatography, and the developing solvent was petroleum ether: ethyl acetate (V / V, 5:1) to obtain 2.26 g of a yellow solid with a yield of 72.9%.
[0097] ESI-MS[M+H] + : m / z 310.4
[0098] 1 H NMR (400MHz, DMSO-d 6 )δppm: 8.02(d,1H,J=8Hz,pyridine-6-H),6.85~7.79(m,11H,Ar-H,pyridi...
Embodiment 3
[0100] Synthesis of N-{2-[benzyl(phenyl)amino]-4-chloro-pyridin-3-yl]formamide (intermediate 5-1)
[0101] Take 8 mL of acetic anhydride and drop it into 20 mL of formic acid solution in which Intermediate 4-1 (3.10 g, 10 mmol) is dissolved at 0°C. After the drop is complete, stir and react at 20°C for 2 h. After the reaction was completed, the solvent was evaporated to dryness, and toluene was added to the residue to remove the solvent by azeotropic evaporation. This was repeated twice to obtain 3.30 g of a white solid with a yield of 97.7%. The product does not need to be purified and can be directly used for the next reaction.
[0102] ESI-MS[M+H] + :m / z 338.7
[0103] 1 H NMR (400MHz, DMSO-d 6 )δppm: 9.17(s,1H,CHO),8.45(s,1H,N H CHO),8.11(d,1H,J=8Hz,pyridine-6-H),6.91~7.85(m,11H,Ar-H,pyridine-5-H),4.51(s,2H,CH 2 ).
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