Pyridinylaminopyridine compounds and preparation methods thereof
A technology of picolylaminopyridines and compounds, applied in the field of picolylaminopyridines
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Embodiment 1
[0079] Example 1 This example illustrates the preparation of compound (02) in Table 1
[0080]
[0081] 2-Chloro-5-chloromethylpyridine (16.10g) and chloroform (60mL) were added to a 250mL three-necked flask equipped with a magnetic stirrer and a drying tube, and after stirring at room temperature for 0.5-1.0hr, 60- 70% ethylamine aqueous solution (18.0 mL) and 20% NaOH aqueous solution (40.0 mL) were added after dropping, benzyltriethylammonium chloride (0.1 g) was added, and the reaction was stirred at room temperature overnight. The pH value was adjusted to weakly alkaline, the organic layer was separated, the aqueous layer was extracted twice with dichloromethane, the organic phases were combined and washed twice with ice brine, and dried over anhydrous sodium sulfate. Concentrate under reduced pressure to obtain 15.9 g of orange-red liquid 2-chloro-5-ethylaminomethylpyridine with a content of 98.5%. GC-MS (M + )(EI,70eV,m / z)(relativeintensity%)calc:170;found:170.
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Embodiment 2
[0083] Example 2 This example illustrates the preparation of compound (08) in Table 1
[0084]
[0085] With reference to the synthetic method of 2-chloro-5-ethylaminomethylpyridine in Example 1, 2-chloro-5-methylaminomethylpyridine was prepared.
[0086] 2,6-dichloro-3-nitropyridine (2.00g), N,N-dimethylformamide (DMF15mL), potassium carbonate (2.87g) were added to a 100mL single-neck flask, and 2 was added dropwise with stirring at room temperature. - The solution of chloro-5-methylaminomethylpyridine (1.60g) in DMF (8.0mL), after dropping, the temperature was raised to 50-80°C and reacted for 3-5hr. After cooling, the reaction solution was poured into 100mL of water, and extracted with ethyl acetate , dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 6-chloro-N-((2-chloropyridin-5-yl)methyl)-N-methyl-3-nitropyridin-2-amine brown sticky solid 3.07 g, content 67.3%. GC-MS (M + ) (EI, 70 eV, m / z) (relative intensity %) calc: 312; found:...
Embodiment 3
[0088] Example 3 This example illustrates the preparation of compound (11) in Table 1
[0089]
[0090] 2,6-dichloro-3-nitropyridine (9.6g) and ethanol (60mL) were added to a 250mL three-necked flask equipped with a magnetic stirring, a constant pressure dropping funnel and a drying tube, and after stirring at room temperature for 15-30min, Add dropwise a solution of sodium ethoxide (3.4g) in ethanol (30mL), drop it in 30-45min, pour it into water after reacting at room temperature for 2-3h, filter and dry to obtain a pale yellow solid 2-chloro-6-ethoxy-3 -Nitropyridine 9.7g, content 80.0%, GC-MS (M + )(EI,70eV,m / z)(relativeintensity%)calc:202;found:202.
[0091] The above-mentioned 2-chloro-6-ethoxy-3-nitropyridine (2.10g) and 15mL of N,N-dimethylformamide (DMF) and potassium carbonate (2.87g) were added to a 100mL single-necked flask, and stirred at room temperature. , add dropwise the DMF (10.0mL) solution of 2-chloro-5-methylaminomethylpyridine (1.60g), after the drop...
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