Method of producing ethyl ether of 3-oxo-3-(2,6-dichloropyridin-3-yl) propanoic acid

FIELD: chemistry.

SUBSTANCE: invention relates to synthesis of 1,3-dicarbonyl compounds and specifically to a method of producing ethyl ether of 3-oxo-3-(2,6-dichloropyridin-3-yl) propanoic acid of formula: . The method involves acylation of potassium 3-oxo-3-ethoxypropanoate with 2,6-dichloronicotinoyl chloride in the presence of anhydrous solvent, ethylamine and magnesium chloride, followed by treatment of the reaction mass with aqueous hydrochloric acid solution and extraction of the end product, characterised by that the solvent used is ethylacetate, where the molar ratio 2,6-dichloronicotinoyl chloride: potassium 3-oxo-3-ethoxypropanoate is equal to 1:1.4-1.6.

EFFECT: high technological effectiveness of synthesis, as well as high output and purity of the disclosed compound.

1 cl, 3 ex

 

The invention relates to the field of synthesis of 1,3-dicarbonyl compounds, particularly to a method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid of the formula:

which finds application as a precursor antibacterial [U.S. Pat. US 3590036, C07D 213/50, C07D 213/61, C07D 213/64, C07D 213/73, C07D 213/74, C07D 213/77, C07D 213/85, C07D 471/04, C07D 213/00, C07D 471/00, (IPC1-7): C07D 39/10. Naphthyridine-3-carboxylic acids, their derivatives and preparation thereof/ since Joey was gone G.Y., D. Gruett - 1971] and antitumor derivatives of 1,8-naphthiridine [Yasunori T. Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 2 [Text] / T. Yasunori, T. Kyoji, S. Koh-ichiro et.al. // J. Med. Chem. - 2004. - Vol. 47. - P. 2097-2109].

A known method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid by the interaction of potassium 3-oxo-3-ethoxypropionate 1-(2,6-dichloronicotinic)-1H-imidazole [Yasunori T. Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 2 [Text] / T. Yasunori, T. Kyoji, S. Koh-ichiro et.al. // J. Med. Chem. - 2004. - Vol.47. - P.2097-2109].

This method is implemented by sequential processing of 2,6-dichloronicotinic acid N,N'-carbonyl diimidazol in a mixture of absolute acetonitrile and tetrahydrofuran with the formation of 1-(2,6-dichloronicotinic)-1H-imidazole. In parallel to the suspension of potassium 2-oxo-3-ethoxypropionate in absolute acetonitrile under ice cooling arr which is anhydrous magnesium chloride and triethylamine and the resulting mixture was stirred for 5 hours. After that, the reaction mass is added prepared as described above, a solution of 1-(2,6-dichloronicotinic)-1H-imidazole in a mixture of absolute tetrahydrofuran and acetonitrile. The reaction was stirred 15 hours. During acidification of the reaction mixture with diluted hydrochloric acid, followed by extractive treatment with ethyl acetate receive technical product with a yield of 93%. Additional purification of the obtained product is achieved by distillation under reduced pressure.

This method has several significant drawbacks. First, its implementation requires the use of 1-(2,6-dichloronicotinic)-1H-imidazole - expensive Alliluyeva agent, obtained in situ from 2,6-dichloronicotinic acid and N,N'-carbonyldiimidazole. Secondly, the synthesis is carried out in a mixture of anhydrous acetonitrile and tetrahydrofuran, and extractive processing is performed using ethyl acetate. The effect of using three different organic solvent forming a mixture, not subject to regeneration. Third, when conducting the synthesis side is the formation of imidazole, which is also not regenerated.

The closest is the method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid by treatment with potassium 3-oxo-3-ethoxypropionate obtained in situ 2,6-d is chloronicotinamide (2,6-dichloronicotinic acid and oxalicacid in dichloromethane) in the presence of magnesium chloride and triethylamine in anhydrous acetonitrile [WO 2008/060693, 22.05.2008]. After removal of the solvent, the reaction mass is diluted with ethyl acetate and treated with hydrochloric acid. The organic phase is separated, washed with saturated sodium chloride solution, dried with sodium sulfate and filtered. After removal of the solvent in vacuum is obtained technical product with a yield of 83%, which is optionally purified by recrystallization from a mixture of methanol and water with the formation of the target substance. The purity of the substance is 95%, and the yield is 74%. Absolutely identical to the method described in other literature [WO 2006/034113, 30.03.2006].

The proposed method has a number of significant shortcomings that reduce its preparative value.

First, to obtain the acid chloride 2,6-dichloronicotinic acid used expensive gloriouse agent - oxalicacid. Secondly, in the synthesis of acid chloride is technical without additional purification that brings in the reaction a lot of additional impurities from the previous process steps.

Secondly, to carry out synthesis is used acetonitrile - toxic solvent which is infinitely miscible with water. This raises the need for prior removal of the solvent from the reaction mixture in vacuum before treatment with hydrochloric acid. This complicates the process in the fission target substance and makes it less effective.

Thirdly, get technical product requires additional cleaning, which further complicates the process and reduces the output.

The objective of the proposed technical solution is the development of a new technological method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid, allowing to carry out the synthesis under mild conditions using available reagents and obtain the desired product in high yield and purity.

The technical result is to increase the ease of synthesis, and an increase in the yield and purity of the claimed compounds.

This technical result is achieved in the method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid of General formula:

involves the acylation of potassium 3-oxo-3-ethoxypropionate 2,6-dichloronicotinic in the presence of an anhydrous solvent, triethylamine and magnesium chloride, followed by treatment of the reaction mixture with an aqueous solution of hydrochloric acid and isolation of the target product, the solvent used ethyl acetate, at a molar ratio of 2,6-dichloronicotinic:potassium 3-oxo-3-ethoxypropionate equal to 1:1.4-1.6.

The essence of the proposed method is the acylation of potassium 3-oxo-ethoxypropionate 2,6-dichloronicotinic in the medium of anhydrous ethyl acetate and acid hydrolysis/decarboxylation of the resulting intermediate of synthesis:

The advantage of this method is the possibility of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid with access, close to quantitative, does not require additional purification. In addition, when carrying out synthesis of available used allerease agent - 2,6-dichloronicotinic, and the synthesis is carried out in ethyl acetate. Thus, the solvent after synthesis and extraction can be almost fully regenerate, and to avoid the costly use of 1-(2,6-dichloronicotinic)-1H-imidazole and N,N'-carbonyldiimidazole.

The proposed method is as follows.

Obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid.

To a suspension of potassium 3-oxo-3-ethoxypropionate in anhydrous ethyl acetate was added anhydrous triethylamine, cool the mixture to 0°C and under stirring was added thereto anhydrous magnesium chloride. The reaction mass is stirred for further 15 minutes under cooling and continue mixing at a temperature of 35-45°C 6 hours then cooled, the resulting suspension to -8°C. To the cooled mixture while stirring for 15 minutes, add a solution of freshly 2,6-dichloronicotinic in anhydrous ethyl acetate. The resulting mixture was stirred for further 1 hour while cooling, and then su is Ki at room temperature, then again cooled to -8°C. To the cooled mixture is slowly poured 12%aqueous solution of hydrochloric acid, stirred for further 30 minutes, the organic phase is separated and the aqueous extracted with ethyl acetate. The combined organic extracts washed with water until neutral environment, dried with anhydrous magnesium sulfate, filtered through a thin layer of silica gel for TLC and removing the solvent on a water bath under reduced pressure. In the remainder of the pure ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid as a viscous oil amber color.

The invention is illustrated by the following examples.

Example 1. Ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid.

To a suspension of 13.6 g (0.08 mol) of potassium 3-oxo-3-ethoxypropionate in anhydrous ethyl acetate (125 ml) was added anhydrous triethylamine (28 ml, 20.3 g, 0.20 mol), cool the mixture to 0°C and under stirring was added thereto anhydrous magnesium chloride (9.1 g, 0.096 mol). The reaction mass is stirred for further 15 minutes under cooling and continue mixing at a temperature of 35-45°C 6 hours then cooled, the resulting suspension to -8°C. To the cooled mixture while stirring for 15 minutes, add a solution of freshly 2,6-dichloronicotinic (12 g, 57 mmol) in anhydrous ethyl acetate (50 ml). The resulting mixture was stirred for further 1 hour while cooling,and then another day at room temperature, then again cooled to -8°C. To the cooled mixture is slowly poured 12%aqueous hydrochloric acid solution (150 ml), stirred for further 30 minutes, the organic phase is separated and the aqueous extracted with ethyl acetate (3 x 75 ml). The combined organic extracts washed with water until neutral environment, dried with anhydrous magnesium sulfate, filtered through a thin layer of silica gel for TLC and removing the solvent on a water bath under reduced pressure. In the remainder of the pure ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid as a viscous oil amber color.

Output - 14.6 g (98%). Rf=0.79 (plate NanoSILGUR 20/UV254, eluent - chloroform - ethyl acetate (4:1, by volume)). The content of the basic substance (by HPLC) - 97.1%.

1H-NMR spectrum (300 MHz, Dl3) δ, ppm, 12.55 - 12.39 (m, 1 H, HE (enol)), 7.97-7.81 (m, 1 H, C4H (aromatic)), 7.38-7.21 (m, 1 H, C5H (aromatic)), 5.74-5.59 (m, 1 H, CH (enol)), 4.25-4.09 (m, 2 H, CH2CH3), 4.05-3.99 (m, 1 H, CH2(keto-form)), 1.32-1.15 (m, 3 H, CH2CH3).

Ratio of initial reagents: 2,6-dichloronicotinic: potassium 3-oxo-3-ethoxypropanol is 1:1.4.

Example 2. Ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid.

Perform analogously to example 1 except the ratio of initial reagents: 2,6-dichloronicotinic: potassium 3-oxo-3-ethoxypropanol composition is given in 1:1.5.

The output of the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid 96%.

Example 3. Ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid.

Perform analogously to example 1 except the ratio of initial reagents: 2,6-dichloronicotinic: potassium 3-oxo-3-ethoxypropanol is 1:1.6.

The output of the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid - 94%.

It follows from the presented examples, the proposed method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid is a technology that allows to obtain the target product under mild conditions using available reagents with high yield and purity.

The method of obtaining the ethyl ester of 3-oxo-3-(2,6-dichloropyridine-3-yl)propanoic acid of General formula

involves the acylation of potassium 3-oxo-3-ethoxypropionate 2,6-dichloronicotinic in the presence of an anhydrous solvent, triethylamine and magnesium chloride, followed by treatment of the reaction mixture with an aqueous solution of hydrochloric acid and isolation of the target product, characterized in that the solvent used in ethyl acetate, with the molar ratio of 2,6-dichloronicotinic:potassium 3-oxo-3-ethoxypropionate is 1:1.4-1.6.



 

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FIELD: organic chemistry, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to compounds inhibiting activity of hormone-sensitive lipase and represented by structure of the formula: (XXXXIVa)

and the formula (XXXXIVb): wherein R1ap and R2ap are chosen independently from (C1-C6)-alkyl, aryl wherein each (C1-C6)-alkyl and aryl can be substituted optionally with one or some substitutes chosen independently from halogen atom, (C1-C6)-alkyl under condition that if R1ap and R2ap are similar then they are not methyl or ethyl, and wherein between substitutes R1ap and R2ap can be a covalent bond optionally, and wherein R5ap, R6ap and R7ap are chosen independently from hydrogen atom and fluorine atom (F), and R4ap is chosen from hydrogen atom, sulfanyl, halogen atom, amino-, nitro-group, (C1-C6)-alkyl, heteroaryl, (C3-C8)-heterocyclyl wherein each among sulfanyl, amino-group, (C1-C6)-alkyl, heteroaryl, (C3-C8)-heterocyclyl can be substituted optionally with one or some substitutes chosen independently from hydroxy-, oxo-group, halogen atom, (C1-C6)-alkyl, aryl, heteroaryl wherein each among (C1-C6)-alkyl, aryl, heteroaryl can be substituted optionally with one or some substituted chosen independently from oxo-group, halogen atom, amino-group, (C1-C6)-alkyl, (C3-C8)-heterocyclyl wherein each among amino-group, (C1-C6)-alkyl, (C3-C8)_heterocyclyl can be substituted optionally with one or some substitutes chosen independently from oxo-group, (C1-C6)-alkyl wherein (C1-C6)-alkyl can be substituted optionally with one or some substitutes chosen independently from oxo-group under condition that R4ap is not methyl. Also, invention relates to a pharmaceutical composition and using these compounds for preparing a medicinal agent used for inhibition of lipolytic activity of hormone-sensitive lipase. Invention describes compounds that can be useful in treatment and prophylaxis of clinical disorders wherein decrease of activity of hormone-sensitive lipase is desirable.

EFFECT: valuable medicinal and biochemical properties of compounds and pharmaceutical composition.

8 cl, 1 tbl, 602 ex

FIELD: chemistry.

SUBSTANCE: compound of formula (I) wherein X represents H or F; Y represents C1-C4 alkyl;C1-C4 alkyl substituted C1-C4 by the group alkoxy; C1-C4 alkyl substituted by the group C1-C4 thioalkoxy, or C2-C3 alkenyl; and agriculturally acceptable salts and esters of carboxylic acid group. The compounds have herbicide potency. The herbicide composition and the method of weed control using the compound of formula (I) are also described.

EFFECT: production of the compound characterized with herbicide potency.

4 cl, 5 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: in general formula (I) , Y represents -CF2(C1-C3 alkyl); W represents -NR1R2, where R1 and R2 independently represent H or C1-C6 alkyl; and acceptable in agriculture carboxyl or 4-aminogroup derivatives. Invention relates to herbicidal composition, containing formula (I) compound and to method of undesirable vegetation control, which includes contacting of vegetation or place of its location with efficient as herbicide amount of compound of formula (I) in item 1, or its application on soil in order to prevent soot emergence.

EFFECT: obtained are novel compounds which can be used as herbicides.

8 cl, 3 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: present invention refers to method of producing diarylamine compound of Formulas , including the stage (1) including formula 21 compound tailing to amine of formula 22 with alkali salt or transition metal catalyst added, and the stage (2) group Y removing from produced compound with acid added: , where radical values are those specified in cl. 1 of formula of invention; as well as to compound of formula (A) or , where X1, X2, X3 and X4 are independently chosen from fluorine and chlorine; and R represents H or methyl.

EFFECT: high-yield production of high purity diaryamines.

49 cl, 9 ex

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