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Synthetic method of Suganon intermediate

A synthetic method and intermediate technology, applied in the field of synthesis of epagliptin intermediates, can solve problems such as low product yield, high cost, and complexity, and achieve simple and easy synthetic method, good product quality, and high yield Effect

Inactive Publication Date: 2017-10-24
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

Method used

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Examples

Experimental program
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Effect test

Embodiment

[0027] Preparation of compound (4)

[0028] Add 20 L of reaction solvent anhydrous toluene and 2.44 kg (10 mol) of compound (2) and 1.62 kg (11 mol) of compound (3) into the 50L reactor at room temperature, then add catalyst tetrakis (triphenylphosphine) Palladium 116 g (0.1 mol) and chiral ligand (S)-(-)-2, 2-bis(xylylphosphine)-1,1-binaphthalene 68 g (0.1 mol), then slowly add 1,8-diazabicycloundec-7-ene (DBU) 1.67 kg (11 mol), after the addition, the temperature was raised to about 50°C, and the reaction was tracked by TLC. After 18 hours, the reaction was completed, and the reaction solution was added to In 20L of 5% ammonium chloride aqueous solution, the liquid was separated, and the organic phase was concentrated under reduced pressure to obtain the crude product of compound (4). The crude product was recrystallized from toluene to obtain 3.13 kg (9.46 mol) of the refined product, with a yield of 94.6%. Purity by HPLC: 97.9% (ee 98.9%).

[0029] 1 H NMR (400 MHz, DMS...

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PUM

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Abstract

The present invention provides a method for synthesizing the intermediate of the compound of formula (1), using the compounds of formula (2) and formula (3) as starting materials, and finally preparing the compound of formula (1) through the following series of reactions The compound, that is, the epagliptin intermediate: Compared with the epagliptin intermediate in the prior art, there are many synthesis steps and the synthesis process is complicated. The synthesis method of the present invention is simple and easy, with low cost and high yield. The product Good quality, 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): C07D209/48
CPCC07D209/48
Inventor 王爱玉
Owner SUZHOU XINEN PHARMA
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