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A kind of preparation method of quinoxide and its hydrochloride

A technology of hydrochloride and methyl acrylate, applied in the field of preparation of quinacetate and its hydrochloride, can solve problems such as curative effect discount, no domestic and foreign literature reports on the synthesis route, etc., and achieves stable quality, simple post-processing, Less side effects

Active Publication Date: 2017-11-17
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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Problems solved by technology

However, with the rapid increase of drug resistance, its efficacy has been greatly reduced, so it is imperative to modify its structure to overcome drug resistance and achieve effective treatment and control of malaria
[0007] Quixite is the impurity A of the antimalarial drug primaquine, and its synthetic route has not been reported in domestic and foreign literature so far.

Method used

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  • A kind of preparation method of quinoxide and its hydrochloride
  • A kind of preparation method of quinoxide and its hydrochloride
  • A kind of preparation method of quinoxide and its hydrochloride

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Embodiment 1

[0023] (1) Synthesis of 4-nitro-methyl pentanoate (compound 3):

[0024] Take nitroethane (compound 1) (225.2g, 3mol), methyl acrylate (compound 2) (86.1g, 1mol) and triethylamine (50.5g, 0.5mol), heat up to 30°C, and continue to stir for reaction 3 day, and then the solvent was distilled off under reduced pressure to obtain viscous compound 3 (104.6 g, 65%). 1 HNMR (CDCl 3 )δ (ppm): 4.631-4.669 (m, 1H, CH), 3.696 (s, 3H, CH 3 O),2.300-2.416(m,2H,CH 2 ),2.058-2.285(m,2H,CH 2 ),1.562-1.579(m,3H,CH 3 ).

[0025] (2) Synthesis of 4-nitro-pentanoic acid (compound 4):

[0026] Add 6mol / L hydrochloric acid (300mL) to compound 3, the product of the previous step, heat to reflux for 4 hours, cool to room temperature, extract with ethyl acetate (3x500mL), combine the organic phases and wash with saturated sodium bicarbonate, and add hydrochloric acid dropwise to the combined aqueous phases to neutralize PH=2, extracted with ethyl acetate (3x500mL), dried over anhydrous sodium su...

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Abstract

The invention discloses quinocide and a preparation method of hydrochloride thereof and belongs to the field of drug chemical research. According to the method, nitroethane and methyl acrylate serve as initial raw materials, and a Michael condensation reaction, formic ester removing, acyl chlorination, amidation, carbonyl reduction, nitro reduction, amino hydrochloric acid salinization and other reactions are sequentially performed so that quinocide and hydrochloride thereof can be prepared. The preparation method is easy to operate, raw materials are low in price, cost is low, the yield is high and reaches 94% or above, and industrial production can be achieved easily.

Description

technical field [0001] The invention relates to a preparation method of quinoxet and its hydrochloride, belonging to the field of medicinal chemistry. Background technique [0002] Quinoxet is an excellent antimalarial drug. The chemical name of quinocide: 8-(4-amino-pentyl) amino-6-methoxy-quinoline (compound 9), the English common name of this compound is Quinocide, structural formula (I), quinocide Hydrochloride (compound 10) structural formula (II): [0003] [0004] Malaria is one of the most deadly parasitic infections. About 250 million people in the world are infected with malaria every year, mainly concentrated in Africa (86%), followed by Southeast Asia (9%) and the Eastern Mediterranean region (3%). In 2006, among the 881,000 malaria deaths, the above three regions accounted for 90%, 4% and 4% respectively. Children under 5 years of age and pregnant women are the groups with the highest malaria incidence and mortality. Malaria is a worldwide infectious dis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 郭晓河陶乐李玉江王强董黎红
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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