A method for preparing rilpivirine hydrochloride isomer z and impurity x and the application of impurity x as pesticide in agriculture
A technology of rilpivirine hydrochloride and rilpivirine, which is used in pesticides, organic chemistry and other directions
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Embodiment 1
[0041] The preparation of embodiment 1 impurity X and isomer Z
[0042] (1) The synthetic method of compound (R is a trifluoroacetyl group) shown in formula III is as follows:
[0043] Add 17.2g of compound 1 shown in formula V into 18ml of acetonitrile, add 10.1g (1eq) of triethylamine, cool to 0°C, add 21g (1eq) of trifluoroacetic anhydride dropwise, control the temperature during the dropping process to less than 30°C, drop After completion of the reaction at room temperature, concentrate the reaction solution, add 200ml of dichloromethane, neutralize with sodium bicarbonate solution, wash with water and saturated sodium chloride, dry over anhydrous magnesium sulfate, filter, concentrate the filtrate, add isopropyl The alcohol was recrystallized, crystallized at 0-5°C, filtered, and dried under reduced pressure at 40-50°C to obtain 21.4g, with a yield of 80%.
[0044] (2) Synthesis of Z-isomer impurity and impurity X
[0045] Add 13.4 g of the compound shown in formula II...
Embodiment 2
[0062] The preparation of embodiment 2 impurity X and isomer Z
[0063] (1) The synthetic method of compound (R is trifluoromethanesulfonyl) shown in formula III is as follows:
[0064] Add 17.2 g of compound 1 shown in formula V into 20 ml of tetrahydrofuran, add 10.1 g (1 eq) of triethylamine, cool to -5°C, add 28.2 g (1 eq) of trifluoromethanesulfonic anhydride dropwise, and control the temperature during the dropping process to less than 10 ℃, dripping is completed, the reaction at room temperature is completed, the reaction solution is concentrated, 300ml of ethyl acetate is added, neutralized with sodium bicarbonate solution, washed with water and saturated sodium chloride, dried overnight with anhydrous magnesium sulfate, filtered, the filtrate is concentrated, and the concentrate Add acetone for recrystallization, crystallize at 0-5°C, filter, and dry under reduced pressure at 40-50°C to obtain 26.1g, yield 86%.
[0065] (2) Synthesis of Z-isomer impurity and impurity...
Embodiment 3
[0067] The preparation of embodiment 3 impurity X and isomer Z
[0068] (1) The synthetic method of compound (R is p-toluenesulfonyl) shown in formula III is as follows:
[0069] Add 17.2g of compound 1 shown in formula V into 30ml of acetone, add 10.1g (1eq) of triethylamine, cool to 0°C, add 19g (1eq) of p-toluenesulfonyl chloride dropwise, and control the temperature during the dropping process to less than 10°C After completion of the reaction at room temperature, the reaction solution was concentrated, 500ml of methyl tert-butyl ether was added, neutralized with sodium bicarbonate solution, washed with water and saturated sodium chloride, dried overnight with anhydrous magnesium sulfate, filtered, the filtrate was concentrated, concentrated The product was recrystallized by adding acetone, crystallized at 0-5°C, filtered, and dried under reduced pressure at 40-50°C to obtain 26.7g, with a yield of 82%.
[0070] (2) Synthesis of Z-isomer impurity and impurity X
[0071] ...
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