High morpholine compound, preparation method, pharmaceutical composition and application
A high morpholine and compound technology, applied in the field of medicine, can solve the problems of serious toxic and side effects, low inhibitory activity, lack of specificity of anti-tumor drugs, etc., and achieve the effect of good marketization prospects.
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Embodiment 1
[0101] 4-(4-(2-Methyl-1H-benzo[d]imidazol-1-yl)-6-morpholinyl-1,3,5-triazin-2-yl)-1,4-homo Preparation of morpholine:
[0102] 2-Methyl-1H-benzimidazole (0.30g, 2.28mmol), 4-(4,6-dichloro-1,3,5-triazin-2-yl)-1,4-homomorpholine (0.54g, 2.28mmol), potassium carbonate (1.26g, 9.12mmol) was dissolved in DMF (9mL). After addition, stir at room temperature. TLC, add 5mL of water to the reaction solution, filter the precipitate, wash with DMF, dry to obtain 0.05g (yield 6.4%) 4-(4-chloro-6-(2-methyl-1H-benzo[d] imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine;
[0103] Take 4-(4-chloro-6-(2-methyl-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-yl)morpholine (0.03g, 0.08 mmol) in homomorpholine (0.30g, 2.97mmol), added, heated to reflux for reaction, cooled, diluted with water, TLC, filtered with suction to obtain 0.02g (yield 64.0%) 4-(4-(2-methyl -1H-benzo[d]imidazol-1-yl)-6-morpholinyl-1,3,5-triazin-2-yl)-1,4-homomorpholine.
[0104] The target product that makes is detected, and its ...
Embodiment 2
[0108] 2-(Difluoromethyl)-4-methoxy-1-(4-morpholinyl-6-(1,4-homomorpholinyl-4-yl)-1,3,5-triazine- Preparation of 2-yl)-1H-benzo[d]imidazol-6-amine:
[0109] 2-Methoxy-4-nitroaniline (20g, 120mmol), glacial acetic acid (60mL), stirred in an ice bath, slowly added concentrated sulfuric acid (100mL) dropwise, controlled temperature 0-10°C in an ice bath, and Mixed acid (70% nitric acid (7.8mL, 120mmol) and concentrated sulfuric acid (4.6mL, 80mmol)) was added dropwise to the system, and after the drop was completed, the reaction was continued at 0-10°C with stirring for 15min, and the temperature was raised to room temperature to continue the reaction, monitored by TLC. After completion, the system was poured into ice water, stirred for 20 minutes, filtered with suction, washed with water, and dried. 4,6-Dinitroaniline.
[0110] Dissolve 2-methoxy-4,6-dinitroaniline (8g, 37.5mmol) in triethylamine (24mL) and acetonitrile (20mL), then add 10% Pd / C (0.37g), and cool to 15°C, add...
Embodiment 3
[0120] 2-(Difluoromethyl)-4-methoxy-1-(4-((3-morpholinyl)amino)-6-(1,4-homomorpholinyl-4-yl)-1 , Preparation of 3,5-triazin-2-yl)-1H-benzo[d]imidazol-6-amine:
[0121] Dissolve anhydrous sodium carbonate (0.53g, 5mmol) in water (6mL), stir to dissolve, add cyanuric chloride (0.92g, 5mmol) at 0°C, stir evenly, and homomorpholine (0.51g, 5mmol) of water (1.25mL) solution was slowly dripped into the above system, the dropwise addition was completed, the temperature was controlled at 0-5°C, and the reaction was carried out for 4h. After suction filtration and washing with water, 0.008g (yield 0.65%) of 4- (4,6-dichloro-1,3,5-triazin-2-yl)-1,4-homomorpholine;
[0122] Replace 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine with 4-(4,6-dichloro-1,3,5-triazin-2-yl )-1,4-homomorpholine, homomorpholine is replaced by N-(3-aminopropyl) morpholine, and all the other required raw materials, reagents and preparation methods are the same as in Example 2, and obtain the product 2 of yield 51...
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