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With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 85 - 95℃; for 20h;Inert atmosphere; Green chemistry;
Under nitrogen atmosphere, ethyl acetate (360 mL) was added with 18.2 g of 5,6-dihydro-3-(4-morpholinyl)-2(1H)-pyridone andEthyl [(4-methoxyphenyl)hydrazino]chloroacetate 30.8 g, 19.4 g of diisopropylethylamine was added under stirring, and the reaction was heated to 85 to 95°C and stirred for 20 hours. After cooling to 15 to 25° C., 35 mL of trifluoroacetic acid was added dropwise after filtration, followed by stirring at 15 to 25° C. for 2 hours.Adding 10percent sodium bicarbonate solution to quench the mass percentage (the mass percentage refers to the percentage of sodium bicarbonate in the total mass of aqueous sodium bicarbonate, the same below), and then extracted with ethyl acetate 1 Times.The organic phase was washed with a 10percent by weight aqueous solution of sodium bicarbonate and a 15percent by weight saline solution (the mass percent containedThe amount refers to the percentage of sodium chloride in the total mass of the saline solution) and is dried over anhydrous sodium sulfate.Filtration and concentration in vacuo (45-55°C, -0.085 MPa--0.1 MPa) afforded a yellow solid.The yellow solid was added to 150 mL of ethyl acetate, heated to 75-85°C and stirred for 1 hour to dissolve, cooled to 0-5°C and stirred for 2 hours, filtered, washed with 0-5°C ethyl acetate, and dried at -0.01. Vacuum drying at MPa--0.1MPa, 45-55°C for 8 hours to 12 hours to obtain a pale yellow solid25.6 g, yield 81.2percent, HPLC purity 98.30percent.
At room temperature, compound D (for example, 4.7 mmol) and 3-morpholino -5,6-dihydro-pyridine -2 (1H)-one (for example, 0.94 g, 5.2 mmol) is added to the reaction flask (for example, 100 ml) in, then adding toluene (for example, 20 ml) and triethylamine. After the completion of the addition, the resulting mixture is heated to 100 °C, the reaction to reflux 12 hours. The resulting mixture to cool to room temperature, concentrated. To the residue add dichloromethane (for example, 20 ml), at room temperature the acid adds by drops trifluoroacetic acid (for example, 5.0 ml). The resulting stirring reaction mixture of 2 hours. After the completion of the reaction, the resulting mixture is concentrated under reduced pressure. After the completion of the concentration, to the resulting added in the mixture of ethyl acetate and purified water (appropriate amount). Stirring the resulting mixture, precipitated solid. Filtering the mixture obtained, the filter cake drying under reduced pressure, to obtain the product, yield by about 30percent.
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In dimethyl sulfoxide; at 110℃; for 12h;Inert atmosphere;
(33 mmol) of the compound of the formula (II) and 6.8 g (36 mmol) of the compound of the formula (III) were added to 160 mL of dimethylsulfoxide,(3.4 mmol) of CuI, 13.7 g (100 mmol) of anhydrous potassium carbonate, 0.66 g (3.6 mmol) of o-phenanthroline, protected by nitrogen, 110 C for 12 h, The aqueous layer was extracted three times with methylene chloride. The organic layers were combined, dried and concentrated to give the crude product (11 g) in the form of a colorless oil, which was obtained in a yield of 93%, recrystallized from ethanol, To give 9.7 g of the compound of the formula (IV) in the form of off-white needle crystals in a yield of 86% and a purity of 99.7%.
1-(4-methoxyphenyl)-7a-(morpholin-4-yl)-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-formic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With triethylamine; In ethyl acetate; at 80℃; for 5h;
100 g (0.55 mol) of intermediate (3) and 170 g (0.132 mol) of intermediate (5) were dissolved at500 ml of ethyl acetate,After adding 310 ml (2.20 mol) of triethylamine, the temperature was raised to 80 ° C and the reaction was completed after 5 h of TLC.Cooled to room temperature, static precipitation of solid.Filtered to give a yellow solid which was washed with diethyl ether (2 X 300 ml), washed with water (2 X 400 ml) and dried to give 176.7 g (theoretical yield 220.9 g) as a yellow solid. Yield 80percent
With palladium diacetate; caesium carbonate; In dimethyl sulfoxide; at 20℃; for 6h;Inert atmosphere;
To a 10 L reaction flask was added 215 g (0.71 mol) of 1- (4-iodophenyl) -2-piperidone, 5,6-dihydro-3- (4- (0.24 mol), 463.6 g (1.42 mol) of cesium carbonate, 3.0 L of DMSO, 3.0 g (0.021 mol) of palladium acetate was added under stirring, and the reaction was carried out at room temperature for about 6 hours , HPLC detection, raw material reaction completely. The system cooled to 5 C and add 15% ammonia water 3.2L and ethyl acetate 3.2L, the system room temperature to continue mixing 3-6h. The filtrate was separated and the aqueous layer was extracted with ethyl acetate 3X1 L. The organic layers were combined, dried, filtered and the solvent was separated to give the crude product 249.5 g, which was recrystallized from methanol and methylene chloride to give the pure compound VIII5,6- 3- (4-morpholinyl) -1- [4- (2-oxo-1-piperidinyl) phenyl] -2 (1H) -pyridone 234.6 g, Yield: 93.0% HPLC: 99.4%
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