WO2010122794A1 - Procédé de production d'un dérivé d'acide pyrazine-carboxylique et intermédiaire pour la production - Google Patents

Procédé de production d'un dérivé d'acide pyrazine-carboxylique et intermédiaire pour la production Download PDF

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Publication number
WO2010122794A1
WO2010122794A1 PCT/JP2010/002898 JP2010002898W WO2010122794A1 WO 2010122794 A1 WO2010122794 A1 WO 2010122794A1 JP 2010002898 W JP2010002898 W JP 2010002898W WO 2010122794 A1 WO2010122794 A1 WO 2010122794A1
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Prior art keywords
alkyl group
producing
acid derivative
pyrazinecarboxylic acid
general formula
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English (en)
Japanese (ja)
Inventor
雅次 織田
幸生 森下
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to a method for producing a 3-haloalkylpyrazine-2-carboxylic acid derivative useful as an intermediate for pharmaceuticals, agricultural chemicals and the like, in particular, as an intermediate for producing agricultural and horticultural acaricides and fungicides, its synthetic intermediate
  • the present invention relates to a method for producing a synthetic intermediate.
  • the 3-haloalkylpyrazine-2-carboxylic acid derivative is used as an intermediate for pharmaceuticals, agricultural chemicals, etc., especially for agricultural and horticultural acaricides (for example, see Patent Document 1) and fungicides (for example, see Patent Document 2). ).
  • a method for producing pyrazine derivatives a method for synthesizing pyrazine derivatives by reacting haloketone derivatives with trifluoromethanesulfonic acid anilide to lead to imino derivatives, then reacting with 1,2-ethylenediamine and further oxidizing is reported.
  • An object of the present invention is to provide a novel and industrially advantageous production method for pyrazinecarboxylic acid derivatives, particularly 3-haloalkylpyrazine-2-carboxylic acid derivatives useful as intermediates for pharmaceuticals and agricultural chemicals.
  • the inventors of the present application reacted a haloester derivative having a specific structure with an alkali metal azide salt, 1,2-ethylenediamine or its acid salt and a dehydrogenating agent.
  • a haloester derivative having a specific structure with an alkali metal azide salt, 1,2-ethylenediamine or its acid salt and a dehydrogenating agent.
  • the imino derivative which is a production intermediate was found to be a novel compound not described in the literature, and the present invention was completed.
  • an objective compound can be produced efficiently and economically on an industrial scale by using an easily available reagent.
  • R 1 is a halo (C 1 -C 6 ) alkyl group, preferably a fluoro (C 1 -C 6 ) alkyl group, particularly preferably fluoro (C 1 -C 3 ).
  • An alkyl group most preferably a trifluoromethyl group and a difluoromethyl group.
  • R 2 is preferably a (C 1 -C 6 ) alkyl group.
  • X is a halogen atom, preferably a bromine atom or a chlorine atom, and most preferably a chlorine atom.
  • M is preferably a lithium atom, a sodium atom or a potassium atom, particularly preferably a sodium atom.
  • halogen atom is fluorine atom, chlorine atom, bromine atom or iodine atom.
  • (C 1 -C 6 ) alkyl group means a linear or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, An alkyl group such as n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, etc., which may be the same as or different from the “halo (C 1 -C 6 ) alkyl group” 1 represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms, and “fluoro (C 1 -C 6 ) alkyl group” is one or more fluorine atoms Substituted or straight chain or branched alkyl group having 1 to 6 carbon atoms
  • fluoro (C 1 -C 3 ) alkyl group represents a linear or branche
  • the “alkali metal atom” refers to a lithium atom, a sodium atom, or a potassium atom.
  • the acid in the acid salt include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, organic acids such as formic acid, acetic acid, trifluoroacetic acid and propionic acid, methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid. And sulfonic acids.
  • reaction involved in the present invention is illustrated as follows.
  • One preferred embodiment of the present invention is the one-pot reaction described below.
  • a reaction between a haloester derivative represented by the general formula (II) or a hydrate thereof, an alkali metal azide salt represented by the general formula (III), 1,2-ethylenediamine or an acid salt thereof, and a dehydrogenating agent By doing so, a pyrazinecarboxylic acid derivative represented by the general formula (I) can be produced.
  • Acid salts for example, salts with inorganic acids such as hydrochloric acid and sulfuric acid, salts with organic acids such as formic acid, acetic acid and propionic acid, or salts with sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and toluenesulfonic acid
  • a dehydrogenating agent to produce a pyrazinecarboxylic acid derivative represented by the general formula (I).
  • the haloester derivative represented by the general formula (II) may be used as it is, it can also be used favorably in the form of a hydrate.
  • the alkali metal azide salt is preferably lithium azide, sodium azide or potassium azide, more preferably sodium azide.
  • the alkali metal azide salt can be used in a range of 0.1 to 10 times mol, preferably 1 to 5 times mol of the haloester derivative represented by the general formula (II) or a hydrate thereof. The range is more preferably 1.0 to 2.5 times mol.
  • 1,2-ethylenediamine or an acid salt thereof can be used in a range of 0.1 to 10-fold moles relative to the haloester derivative represented by the general formula (II) or a hydrate thereof, preferably 0
  • the range is from 5 to 5 times mol, and more preferably from 0.9 to 1.2 times mol.
  • the dehydrogenating agent is not particularly limited as long as it has a dehydrogenating ability.
  • manganese compounds such as manganese dioxide; chromic acids such as sodium chromate; lead compounds such as lead tetraacetate; mercury compounds such as mercury oxide;
  • Oxidizing agents such as osmium tetroxide, ruthenium tetroxide and selenium dioxide; metal halides such as iron chloride, copper iodide and copper chloride; halogens such as iodine and bromine; N-chlorosuccinimide, N-bromosuccinimide and diiodo Haloimides such as hydantoin; transition metal compounds such as palladium, platinum, iridium, rhodium, ruthenium, selenium, rhenium; quinone-based oxidizing agents such as DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone); Peroxides
  • the metal compound such as palladium, platinum, iridium, rhodium, ruthenium, selenium, rhenium
  • the metal itself can also be used. C., 1997, 62, 1072-1078, TL, 48 (2007) 2729-2732), and palladium and platinum supported on activated carbon are preferable.
  • transition metal compounds 230-243 can also be used.
  • transition metal compounds are zero-valent, formic acid salts such as sodium formate and ammonium formate; hydroquinone, formaldehyde, etc. in order to carry out the reaction while returning the transition metal compound oxidized in the reaction to zero-valent (reduced type)
  • Organic reducing agents such as formic acid, glucose, and ascorbic acid; reducing gases such as carbon monoxide, ethylene, and methane can also be mixed and used.
  • transition metal compounds in an oxidized state can also be used.
  • PdCl 2 , Pd (OH) 2 palladium oxide, palladium sulfide, Pt / O 2 , iridium chloride (III), rhodium chloride (III), ruthenium chloride.
  • inorganic transition metal compounds such as rhenium oxide; palladium (II) acetate, dichlorobis (benzonitrile) palladium (II), dichlorobis (trialkylphosphine) palladium (II), trans- [iodo (phenyl) bis (dimethyl) Phenylphosphine) palladium (II)], trans- [dimethylbis (triphenylphosphine) palladium (II)], (dioxygen) bis (t-butyl isocyanate), Pd 2 Cl 4 (C 2 H 4 ) 2 , Pd 2 Cl 4 (PPh 3 ) 2, Pd ( 2 H 4) (PPh 3) 2, PdCl 2 (C 8 H 12), [PdCl (C 3 H 5)] 2, Pd (C 3 H 5) (C 5 H 5), Pd (C 3 H 5 ) 2 , [Pd (C 5 H 5 ) (C 8 H 12 )] BF 4
  • Two or more transition metal compounds can also be used in combination, for example, a technique such as Wacker oxidation (“Palladium Reagents and Catalysis”, First Edition 2004, Wiley, 29-35; Synthesis 1984, 369-384). Can be used.
  • dehydrogenating agents can be used in the range of 0.001 to 10-fold mol, preferably in the range of 0.01 to 5-fold mol based on the haloester derivative represented by the general formula (II). is there.
  • the inert solvent used is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane
  • aromatics such as benzene, toluene, xylene, and chlorobenzene.
  • Hydrocarbons Halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; Linear or cyclic ethers such as diethyl ether, t-butyl methyl ether, dioxane, tetrahydrofuran, and 1,2-dimethoxyethane; Methanol, ethanol , N-propanol, 2-propanol, n-butanol, s-butanol, t-butanol and other alcohols; esters such as ethyl acetate; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile Examples of the inert solvent include 1,3-dimethyl-2-imidazolidinone, pyridine, acetic acid, and water. These solvents may be used alone or in admixture of two or more kinds of inert solvents. it can.
  • Examples of the purpose of adjusting the pH in the reaction system include organic bases such as triethylamine, tributylamine, pyrrolidine, piperidine, morpholine, pyridine, 3-picoline, 4-picoline, 4-dimethylaminopyridine; lithium hydroxide, Alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; Alkali metal alkoxides such as sodium methoxide and sodium ethoxide; Carbonates such as sodium hydrogen carbonate and potassium carbonate; Potassium monohydrogen phosphate and trisodium phosphate Phosphates such as sodium formate and sodium acetate; inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid; organic acids such as formic acid, acetic acid, trifluoroacetic acid and propionic acid; methanesulfonic acid and trifluoromethanesulfonic acid P-Toluenesulfonic acid It is possible to use the sulfonic
  • phase transfer catalyst such as a quaternary ammonium salt such as tetrabutylammonium chloride or a crown ether such as 18-crown-6 can be used, and is represented by the general formula (II).
  • the amount can be appropriately selected within the range of 0.001 to 0.1 moles relative to the haloester derivative.
  • the reaction temperature may be appropriately selected within the range of ⁇ 20 ° C. to the reflux temperature of the inert solvent used, but is preferably selected from the range of 0 ° C. to 120 ° C.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 100 hours.
  • the pyrazinecarboxylic acid derivative represented by the general formula (I) may be isolated from the reaction system containing the target product by a conventional method. If necessary, this may be recrystallized, column chromatography, distillation, etc.
  • the desired product can be produced by purifying with
  • Another preferred embodiment of the present invention is the stepwise reaction described below.
  • (a) a haloester derivative represented by the general formula (II) or a hydrate thereof and an alkali metal azide salt represented by the general formula (III) are reacted stepwise in an inert solvent, Derived into an imino form represented by the general formula (IV) or a hydrate thereof, then (b) reacted with 1,2-ethylenediamine or an acid salt thereof, and finally (c) a dehydrogenating agent is allowed to act.
  • a pyrazinecarboxylic acid derivative represented by the general formula (I) can be produced.
  • the reactions (a), (b) and (c) may be performed according to the method described in 1). Even if each reagent is added simultaneously as described in 1) or sequentially as described in 2), the desired product can be obtained satisfactorily.
  • the compound represented by the general formula (II) can be produced by a known method, for example, the method described in Helvetica Chumica Acta (1965), 48 (6), 1423-6, or the like. Further, the 3-haloalkylpyrazine-2-carboxylic acid derivative obtained by the production method of the present invention can be easily produced by, for example, the method shown in Reference Examples, etc. ) And the like can be produced.
  • Example 1 Preparation of ethyl 3-trifluoromethylpyrazine-2-carboxylate To a 4 mL aqueous solution of sodium azide (2.6 g, 40 mmol) and 1,2-ethylenediamine hydrochloride (3.2 g, 24 mmol) in 2-chloro-4,4 , A solution of ethyl 4-trifluoro-3-oxobutanoate (4.4 g, 20 mmol) in ethyl acetate (8 mL) was added dropwise. Thereafter, 5% Pd / C (2 g; 50% wet) and ethyl acetate (2 mL) were added, and the mixture was stirred at room temperature for 1 hour.
  • reaction mixture was then stirred at 35 ° C. for 1 hour and then heated to reflux for 2.5 hours.
  • the reaction was cooled to room temperature.
  • Ethyl acetate (100 mL) and water (60 mL) were added, Pd / C was removed by filtration, and the mixture was extracted with ethyl acetate.
  • the organic layer was washed with water and dried, the solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain ethyl 3-trifluoromethylpyrazine-2-carboxylate.
  • Example 2 Preparation of ethyl 3-trifluoromethylpyrazine-2-carboxylate To a mixed solution of sodium azide (2.6 g, 40 mmol) and tetrabutylammonium chloride (0.6 g, 2 mmol) in toluene (6 mL) and water (4 mL) A toluene solution (2 mL) of ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate (4.4 g, 20 mmol) was added dropwise.
  • Example 3 Production of ethyl 3-difluoromethylpyrazine-2-carboxylate Sulfuryl chloride (8.5 g, 63 mol) was added to ethyl 4,4-difluoro-3-oxobutanoate (10 g, 60 mol), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water (100 ml) and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention a pour objet un procédé nouveau et avantageux sur le plan industriel de production d'un dérivé d'acide pyrazine-carboxylique, particulièrement un dérivé d'acide 3-halogénoalkylpyrazine-2-carboxylique, composé utile en tant qu'intermédiaire pour la production d'un agent pharmaceutique, d'un agent agrochimique et analogues. L'invention a pour objet spécifique un procédé de production d'un dérivé d'acide pyrazine-carboxylique représenté par la formule générale (I), qui est caractérisé par la réaction d'un dérivé d'halogénoester représenté par la formule générale (II) avec un sel azoture de métal alcalin représenté par la formule générale (III), de la 1,2-éthylènediamine ou l'un de ses sels d'acide et un agent de déshydrogénation.
PCT/JP2010/002898 2009-04-23 2010-04-22 Procédé de production d'un dérivé d'acide pyrazine-carboxylique et intermédiaire pour la production Ceased WO2010122794A1 (fr)

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JP2009-104861 2009-04-23
JP2009104861 2009-04-23

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018041853A1 (fr) 2016-09-01 2018-03-08 Lonza Ltd Procédé de préparation d'esters d'acide 3- (trifluorométhyl) pyrazine-2-carboxylique
CN108069915A (zh) * 2016-11-15 2018-05-25 华中师范大学 一种吡嗪酰胺类化合物及其制备方法和应用以及一种杀菌剂
CN109096209A (zh) * 2017-06-20 2018-12-28 华中师范大学 吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666004A (zh) * 2017-10-13 2019-04-23 华中师范大学 含有三氟甲基的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666003A (zh) * 2017-10-13 2019-04-23 华中师范大学 含碘元素的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109689631A (zh) * 2016-09-01 2019-04-26 隆萨有限公司 制备3-（三氟甲基）吡嗪-2-甲酸酯的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005115994A1 (fr) * 2004-05-27 2005-12-08 Nihon Nohyaku Co., Ltd. Dérivés anilides d'acides pyrazinecarboxyliques substitués ou sels de ceux-ci, intermédiaires de ceux-ci, pesticides à usage agricole et horticole et utilisation de ceux-ci
WO2007072999A1 (fr) * 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Derives pyrazinecarboxamide et agents de lutte contre les parasites les contenant

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005115994A1 (fr) * 2004-05-27 2005-12-08 Nihon Nohyaku Co., Ltd. Dérivés anilides d'acides pyrazinecarboxyliques substitués ou sels de ceux-ci, intermédiaires de ceux-ci, pesticides à usage agricole et horticole et utilisation de ceux-ci
WO2007072999A1 (fr) * 2005-12-22 2007-06-28 Nihon Nohyaku Co., Ltd Derives pyrazinecarboxamide et agents de lutte contre les parasites les contenant

Non-Patent Citations (1)

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Title
RAYMOND J. BERGERON ET AL.: "Application of N-Phenyltrifluoromethanesulfonamides to the Synthesis of Pyrazines", JOURNAL OF ORGANIC CHEMISTRY, vol. 45, no. 1, 1980, pages 161 - 163 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018041853A1 (fr) 2016-09-01 2018-03-08 Lonza Ltd Procédé de préparation d'esters d'acide 3- (trifluorométhyl) pyrazine-2-carboxylique
CN109689631A (zh) * 2016-09-01 2019-04-26 隆萨有限公司 制备3-（三氟甲基）吡嗪-2-甲酸酯的方法
CN108069915A (zh) * 2016-11-15 2018-05-25 华中师范大学 一种吡嗪酰胺类化合物及其制备方法和应用以及一种杀菌剂
CN108069915B (zh) * 2016-11-15 2020-05-15 华中师范大学 一种吡嗪酰胺类化合物及其制备方法和应用以及一种杀菌剂
CN109096209A (zh) * 2017-06-20 2018-12-28 华中师范大学 吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109096209B (zh) * 2017-06-20 2022-03-01 华中师范大学 吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666004A (zh) * 2017-10-13 2019-04-23 华中师范大学 含有三氟甲基的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666003A (zh) * 2017-10-13 2019-04-23 华中师范大学 含碘元素的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666003B (zh) * 2017-10-13 2020-08-21 华中师范大学 含碘元素的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂
CN109666004B (zh) * 2017-10-13 2020-08-21 华中师范大学 含有三氟甲基的吡嗪酰胺类化合物及其制备方法和应用以及杀菌剂

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