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Application of asymmetric conjugate addition reaction in synthesis of Imigliptin intermediate compound

A technology of conjugated addition and intermediates, which is applied in the field of synthesis of epagliptin intermediates, can solve the problems of low product yield, high cost, poor quality, etc., and achieve simple synthesis methods, good product quality, low cost effect

Inactive Publication Date: 2017-11-28
SUZHOU XINEN PHARMA
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Problems solved by technology

[0009] In the prior art, the synthesis process of epagliptin intermediates is often more complicated, the cost is higher, and there are also defects of low product yield and poor quality, which cannot be suitable for industrialized large-scale production

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  • Application of asymmetric conjugate addition reaction in synthesis of Imigliptin intermediate compound

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Embodiment

[0028] Preparation of compound (3)

[0029] Add 20 L of reaction solvent anhydrous dichloromethane and 2.6 kg (10 mol) of compound (2) and 1.2 kg (11 mol) of phenylhydroxylamine to the 50L reactor at room temperature, then add catalyst 84 g (0.1 mol) After the addition, the temperature was raised to reflux, TLC followed the reaction, and the reaction was completed after 22 hours. The reaction solution was added to 20L 5% ammonium chloride aqueous solution, separated, and the organic phase was concentrated under reduced pressure to obtain the crude product of compound (3). The crude product was washed with toluene 3.5 kg (9.49 mol) of the refined product were obtained by recrystallization, and the yield was 94.9%. Purity by HPLC: 97.4% (ee 98.7%).

[0030] 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.24 – 7.05 (m, 2H), 6.97 – 6.83 (m, 1H),6.83 – 6.73 (m, 3H), 6.61 (m, 1H), 3.51 (m, 1H), 3.39 – 3.08 (m, 3H ), 2.82(m, 1H), 2.72 – 2.47 (m, 2H), 1.61 (s, 1H), 1.35 (t, J = 6.6 Hz, 3H). ...

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Abstract

The present invention provides a method for synthesizing a compound of formula (1) igliptin intermediate. The compound of formula (2) is used as a starting material, and the compound of formula (1) is finally prepared through the following series of reactions, that is, the Ilogliptin intermediate: Compared with the prior art, the Ilogliptin intermediate has many synthetic steps and complicated synthesis process. The synthetic method of the present invention is simple and easy to implement, has low cost, high yield and good product quality, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing an epagliptin intermediate, belonging to the technical field of drug synthesis. Background technique [0002] Elogliptin (generic name: EVOGLIPTIN, trade name Suganon), chemical name: (R)-4-((R)-3-amino-4-(2,4,5-trifluorophenyl) butyl Acyl)-3-(tert-butanol ether methyl)piperazin-2-one. The molecular weight of Elogliptin: 401.42; CAS registration number: 1222102-29-5; the structural formula is shown in Formula 1: [0003] [0004] Formula 1 [0005] Elogliptin was developed by Dong-A Pharmaceutical Company in South Korea. On October 2, 2015, it was approved by the Korean Ministry of Food and Drug Safety (MFDS) for the treatment of type 2 diabetes in South Korea. Ilogliptin is a DPP-4 inhibitor drug for the treatment of type 2 diabetes. Dosage specification: Elogliptin 5mg / tablet. [0006] prior art literature [0007] Non-patent literature: 1: Lab. Invest., 2016, 96, 5, P547-P560; Non-patent li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/22
CPCC07C269/06C07C327/22C07C271/22
Inventor 王爱玉
Owner SUZHOU XINEN PHARMA
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