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A synthesis process, the technology of ticagrelor, applied in the field of synthesis process of ticagrelor intermediates, can solve the problems of no stereoselectivity, expensive raw materials, long steps, etc. Short, the effect of reducing production costs
Inactive Publication Date: 2017-03-15
QINGDAO YUNTIAN BIOTECH
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[0012] Therefore, given the above 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxan-4-yl In the preparation method of ]oxyethanol, there are extensiv
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Embodiment 1
[0033] Synthesis of compounds shown in formula I
[0034] In a 150ml flask, 1.36g (10mmol) ZnCl 2 , 12.11g (100mmol) benzaldehyde oxime, 6.28g (95mmol) cyclopentadiene were added to 60ml 1,4-dioxane, stirred and reacted at 40°C for 6 hours, the reaction was completed, the reaction solution was concentrated, poured into water for cleaning , filtered, and then recrystallized from petroleum ether to obtain 14.75 g of the compound shown in formula I, with a yield of 82.9% and a purity of 99.32%.
Embodiment 2
[0036] Synthesis of compounds shown in formula I
[0037] In a 150ml flask, 2.72g (20mmol) ZnCl 2 , 12.11g (100mmol) benzaldehyde oxime, 5.95g (90mmol) cyclopentadiene were added to 60ml 1,4-dioxane, stirred and reacted at 20°C for 4 hours, the reaction was completed, the reaction solution was concentrated, poured into water for cleaning , filtered, and then recrystallized from petroleum ether to obtain 13.45 g of the compound shown in formula I, with a yield of 79.8% and a purity of 98.97%.
Embodiment 3
[0039] Synthesis of compounds shown in formula I
[0040]In a 150ml flask, 1.33g (10mmol) AlCl 3 , 12.11g (100mmol) benzaldehyde oxime, 5.29g (80mmol) cyclopentadiene were added to 60ml 1,4-dioxane, stirred and reacted at 30°C for 4 hours, the reaction was completed, the reaction solution was concentrated, poured into water for cleaning Three times, filtered, and then recrystallized from petroleum ether to obtain 12.24 g of the compound represented by formula I, with a yield of 81.7% and a purity of 99.03%.
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Abstract
The invention discloses a synthesis process of a ticagrelor intermediate. The synthesis process of the ticagrelor intermediate is characterized by including the steps: 1) under acidic condition, contacting benzaldoxime with cyclopentadiene for reaction so as to obtain a compound shown in formula I; 2) under the catalysis of osmium tetroxide, using hydrogen peroxide to oxidize the compound shown in the formula I so as to obtain a compound shown in formula II; 3) under the catalysis of p-toluenesulfonic acid, reacting the compound shown in the formula II and acetone to obtain a compound shown in formula III; 4) in the presence of an alkali, reacting the compound shown in the formula III with 2-bromoethyl alcohol so as to obtain a compound shown in formula IV; 5) reducing the compound shown in the formula IV so as to obtain the ticagrelor intermediate. The raw materials used here in the method provided herein are low in cost and easy to obtain, so that production cost; the use of chiral materials is not required, a high stereoselectivity product can be acquired through cycloaddition reaction, the steps are short, the reaction yield is very high, and a new approach for the synthesis of ticagrelor is provided.
Description
technical field [0001] The invention belongs to the technical field of medicine synthesis, and relates to a synthesis process of a ticagrelor intermediate. Background technique [0002] Ticagrelor (Ticagrelor), the chemical name is (1S,2S,3R,5S)-3-[7-[(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamino]- 5-(Propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2 -diol, which is the first reversible binding oral P2Y12 adenosine diphosphate receptor antagonist, has a significant inhibitory effect on ADP-induced platelet aggregation, and can effectively improve the symptoms of patients with acute coronary heart disease. The compound was developed by AstraZeneca and approved for marketing in the European Union and the United States in 2010 and 2011 respectively. In addition, the imported tablet has also been approved by the China Food and Drug Administration (SFDA) to be marketed in my country. The specific structural formula of ticagrelor is as foll...
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