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Method for preparing compound UNC1215

A compound and catalyst technology, applied in the field of medicinal chemistry synthesis, can solve the problems of high cost, low yield, dangerous operation, etc., and achieve the effect of easy operation

Inactive Publication Date: 2014-10-01
CHENGDU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to: provide a new method for preparing compound UNC1215, to solve the problems of operation risk, high cost and low yield in the above-mentioned prior art

Method used

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  • Method for preparing compound UNC1215
  • Method for preparing compound UNC1215
  • Method for preparing compound UNC1215

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Embodiment 1

[0032] A method for preparing compound UNC1215, comprising the following steps in turn:

[0033] (1) Nitration reaction: Dissolve 10 g of dimethyl terephthalate (Compound I) in 50 ml of concentrated sulfuric acid under electromagnetic stirring, cool in an ice bath, slowly add 5 ml of fuming nitric acid dropwise into the reaction bottle, and keep the temperature constant Over 20°C; react for 1 hour after the addition, TLC (thin-layer chromatography) monitors the consumption of raw materials, slowly pour the reaction solution into 100ml of ice water with stirring, a white solid precipitates, filter, and filter the cake with saturated NaHCO 3 Washed to pH8, dried to give 10.2g white solid, namely dimethyl 2-nitroterephthalate (compound II), such as figure 1 As shown, the yield is 82.9%, mp: 73-74°C (literature value [Tetrahedron Lett, 2008, 49 (38): 5544 -5547] mp: 73-73.3°C) 1 H NMR ( d 6 -DMSO,400MHz): δ8.49(1H,s), 8.36(1H,dd,J=1.6), 8.02(1H,d), 3.94(3H,s), 3.89(3H,s);

[0...

Embodiment 2

[0039] (1) Nitration reaction: Dissolve 10 g of dimethyl terephthalate (Compound I) in 50 ml of acetic anhydride under electromagnetic stirring, cool in an ice bath, slowly add 5 ml of fuming nitric acid into the reaction flask dropwise, and keep the temperature constant Over 20°C; react for 1 hour after the addition, TLC (thin-layer chromatography) monitors the consumption of raw materials, slowly pour the reaction solution into 100ml of ice water with stirring, a white solid precipitates, filter, and filter the cake with saturated NaHCO 3 Washing to pH 8, drying to obtain 9.9g of white solid, that is, dimethyl 2-nitroterephthalate (compound II), yield 80.5%, mp: 73-74°C (literature value [Tetrahedron Lett, 2008, 49 (38): 5544 -5547]mp:73-73.3℃) 1 H NMR ( d 6 -DMSO,400MHz): δ8.49(1H,s), 8.36(1H,dd,J=1.6), 8.02(1H,d), 3.94(3H,s), 3.89(3H,s);

[0040] (2) Nitro reduction reaction : Add 2.3g of ammonium chloride and 2.3g of iron powder to 50ml of methanol / water solution, sti...

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Abstract

The invention discloses a method for preparing a compound UNC1215, belonging to the technical field of pharmaceutical chemistry synthesis. The method sequentially comprises the following steps: nitration, nitro reduction reaction, Buchwald reaction, esterolysis reaction, condensation reaction and the like. The overall reaction yield can reach 67%, which is higher than the yield (60%) in the document. The method changes the synthesis route, avoids the pipe sealing reaction, sequentially performs the nitration, reduction reaction, Buchwald reaction, hydrolysis reaction and condensation reaction, and is simple to operate.

Description

technical field [0001] The present invention relates to the field of pharmaceutical chemical synthesis, in particular to a method for preparing compound UNC1215. Background technique [0002] Malignant brain tumor (MBT) is a disease that seriously threatens human health. According to the third national death retrospective sampling survey, MBT in the sampling area ranks seventh among malignant tumors, accounting for 2.3% of malignant tumor mortality (the first in the country) Three retrospective sampling survey reports on causes of death, Beijing, Peking Union Medical College Press, 2008:21-23). The L3MBTL3 protein is one of the reverse transcription factors of MBT; while UNC1215, the chemical name is (2-(anilino)-1,4-phenylene)bis((4-(pyrrolidin-1-yl)piperidine-1 -base) ketone), the chemical structure is as follows: [0003] , which is the first chemical probe for the methyllysine (Kme) reading domain of the L3MBTL3 protein. UNC1215 is non-toxic in cells, competitively ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58
CPCC07D211/58
Inventor 陈宇瑛罗刚王瑛瑛刘啸林世博赵圣轩戴川
Owner CHENGDU UNIV