Ticagrelor intermediate and synthesis method thereof
A technology of ticagrelor and a synthesis method, applied in the field of drug synthesis, can solve the problems of being unable to be suitable for industrialized large-scale production, low product yield and high cost, and achieve the effects of novel technical route, good product purity and easy operation.
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[0033] Example 1
[0034] Preparation of compound 4:
[0035] Put 142g (1mol) of compound (2) and 382g (1.05mol) of compound (3) in 1L of dichloromethane into a 2L four-necked round bottom flask, stir at room temperature for 16 hours, filter, concentrate, and recrystallize the crude product from toluene 226g of the prepared intermediate compound (4). The mass yield of compound (4) was 159%, and the purity detected by HPLC was 99.02%.
[0036] 1 H NMR(500MHz, DMSO-d 6 )δ7.69(d,J=30.4Hz,1H), 7.48(m,1H), 7.11(m,1H), 6.93(m,1H), 6.81(d,J=30.1Hz,1H), 3.15( q, J = 13.1Hz, 2H), 1.31 (t, J = 13.2Hz, 3H).
[0037] Preparation of Intermediate Compound 1:
[0038] Add 500 mL of anhydrous dichloromethane as the reaction solvent and 220 g (0.96 mol) of compound (4) to a 2L four-necked round bottom flask, and then add 5.5 g (9.6 mmol) Rh of the catalyst 2 (OCOt-Bu) 4 And ligand 5.6g (9.6mmol), after the addition, the reaction solution was cooled to -30°C, and then a toluene solution of diazomethan...
Example Embodiment
[0042] Example 2
[0043] According to the synthesis method of Example 1, the molar ratio of compound (2) and compound (3) is 1:1.1, the reaction solvent of compound (1) in the preparation is replaced with anhydrous ether, and the rhodium catalyst is RhCl 3 The molar ratio of rhodium catalyst to compound (4) is 1:20, the molar ratio of ligand to rhodium catalyst is 1:1.2, and the reaction temperature is -80°C. Finally, the refined product of compound (1) was obtained, the mass yield was 98.5%, and the purity detected by HPLC was 99.55%.
Example Embodiment
[0044] Example 3
[0045] According to the synthesis method of Example 1, the molar ratio of compound (2) and compound (3) is 1:1.2, the reaction solvent of compound (1) in the preparation is replaced with anhydrous toluene, and the rhodium catalyst is Rh 2 (pfb) 4 The molar ratio of rhodium catalyst to compound (4) is 1:80, the molar ratio of ligand to rhodium catalyst is 1:1.5, and the reaction temperature is 20°C. Finally, the refined product of compound (1) was obtained, the mass yield was 98%, and the purity detected by HPLC was 99.43%.
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