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WO2004069802A1 - Processus de production de pyridine substitee 2-amino-3 - Google Patents

Processus de production de pyridine substitee 2-amino-3 Download PDF

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Publication number
WO2004069802A1
WO2004069802A1 PCT/JP2004/000995 JP2004000995W WO2004069802A1 WO 2004069802 A1 WO2004069802 A1 WO 2004069802A1 JP 2004000995 W JP2004000995 W JP 2004000995W WO 2004069802 A1 WO2004069802 A1 WO 2004069802A1
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WO
WIPO (PCT)
Prior art keywords
copper
production method
catalyst
acid
metal
Prior art date
Application number
PCT/JP2004/000995
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English (en)
Japanese (ja)
Inventor
Yukihito Sumino
Shinobu Wakabayashi
Original Assignee
Shionogi & Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to JP2005504814A priority Critical patent/JPWO2004069802A1/ja
Publication of WO2004069802A1 publication Critical patent/WO2004069802A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals

Definitions

  • the present invention relates to 2-amimino 3-substituted pyridines (eg, 2,3-diaminopyridine) useful as synthetic intermediates such as cefm antibacterial agents and imidazopyridines, or as pharmaceutical raw materials such as organometallic complex ligands. It relates to a method for producing the salt.
  • 2-amimino 3-substituted pyridines eg, 2,3-diaminopyridine
  • synthetic intermediates such as cefm antibacterial agents and imidazopyridines
  • pharmaceutical raw materials such as organometallic complex ligands.
  • 2,3-diaminopyridine is described as a raw material of the 3-position side chain of a septum antibacterial agent (eg, Patent Document 1).
  • Non-Patent Document 1 As a typical production method of 2,3-diaminopyridine, a method of synthesizing in four steps using 2-aminoviridine as a starting material is described (eg, Non-Patent Document 1). However, this method uses metals such as bromine and iron as reaction reagents, which is not desirable in terms of environment and safety, and the yield is as low as 26%, which is not a satisfactory method as an industrial method. . Further, in a production method using 3-ethoxycarbonylamino-2-nitropyridine as a starting material, nickel metal, which is concerned with carcinogenicity, is used (eg, Non-Patent Document 2).
  • Non-Patent Document 3 As a method for synthesizing an aminoviridine derivative using a copper catalyst, an amination reaction between bromopyridine and ammonia is known (eg, Non-Patent Document 3).
  • the amination reaction with chloro-open pyridine which is more inert than bromopyridine, has not been successful.
  • this reaction for example, in the case of 2-chloro-1-5-nitropyridine having an electron-withdrawing substituent that enhances the reactivity of the chromatol group, an aminoviridine derivative is produced.
  • No amination reaction with an aminochloropyridine having an electron donating substituent which weakens the reactivity of the group is described. Also, there is no description of a method for removing a water-soluble copper catalyst which has a risk of water pollution used as a reaction catalyst.
  • Patent Document 1 International Publication No. 0/3 2 6 06
  • Patent Document 2 Japanese Patent Application Laid-Open No. 05-33 39 2 36,
  • Non-Patent Document 1 Barham (W.E.Barham), Organic Synthesis (Org. Syn), USA, Vol. 44, P 34-39 (1964)
  • Non-Patent Document 2 J. W. Clark—Lewins, et al., J. Cheni. Soc., UK, P442—447 (1957)
  • Non-Patent Document 3 Lang et al., Tett. Lett, USA, Vol. 42, P3251-3254 (2001) Disclosure of the invention
  • R is NHR 1 N (R 1) 2 , OH, 0 R J s NH CO CH 3, SR 1 (wherein, R 1 is alkyl), a manufacturing method of claim 1, wherein the.
  • the production method of the present invention is constituted or selected from the following three steps.
  • the first step is to react the 3-substituted 1-2-halogenobilizine (I) with ammonia in the presence of a catalyst, preferably a copper catalyst, to form 2-
  • a catalyst preferably a copper catalyst
  • the second step is a method of removing copper from the reaction mixture of the first step by treating it with a sulfide compound.
  • the first step is a method of reacting compound (I) with ammonia in the presence of a catalyst to produce 2-amino-1-substituted pyridine (II), preferably 2,3-diaminopyridine.
  • the halogen is preferably c including fluorine, chlorine, bromine and iodine, and particularly preferably chlorine.
  • the catalyst is preferably a catalyst containing a metal such as cobalt, tin, zinc, iron, aluminum, boron, copper, titanium, arsenic, thallium, nickel, chromium, rhodium, iridium, platinum, palladium, etc.
  • a metal-containing catalyst is preferably a metal exhibiting a coordination property to the N atom and R of pyridine of the compound (I).
  • the catalyst is preferably a catalyst containing copper (hereinafter, referred to as a copper catalyst).
  • the copper catalyst includes, for example, copper salts, copper oxides, metallic copper and mixtures thereof, and further includes complex salts composed of copper salts, copper oxides, metallic copper or mixtures thereof and organic bases.
  • Copper salts include cuprous chloride, cuprous bromide, cupric chloride, cupric bromide, anhydrous cupric nitrate, cupric nitrate heptahydrate, anhydrous copper sulfate and copper sulfate pentahydrate Japanese products.
  • copper oxide include cuprous oxide and cupric oxide.
  • copper salts particularly preferably copper halides, such as cuprous chloride (CuCl).
  • CuCl cuprous chloride
  • the amount of the copper catalyst to be used is generally in the range of 0.01 to 5 equivalents, preferably 0.01 to 0.5 equivalents, particularly preferably 0.1 to 0.4 equivalents, relative to compound (I). Is equivalent.
  • This reaction is preferably performed in an aqueous ammonia solution, but may be performed in a polar solvent or an organic base may be added to the reaction solution.
  • Ammonia used in the amination reaction includes ammonium acetate, ammonium picocarbonate, ammonium benzoate, ammonium carbonate, ammonium formate, ammonia oxalate, aqueous ammonia, and the like. And liquid ammonia.
  • the ammonia is preferably ammonia water having a concentration of 1 to 50%, particularly preferably an aqueous ammonia solution having a concentration of 20 to 30%.
  • the amount of ammonia to be used is generally 1 to 100 equivalents, preferably 2 to 50 equivalents, particularly preferably 3 to 30 equivalents, relative to compound (I).
  • polar solvent examples include cyclic amides such as 1-methyl-1-pyrrolidinone, cyclic ureas such as 1,3-dimethyl-12-imidazolidinone, sulfoxides such as dimethyl sulfoxide, and dimethyl sulfone and sulfolane.
  • ethers such as 1,4-dioxane, N, N —Dialkyl anilines such as dimethyl aniline and N, N-Jetyl aniline; heterocyclic compounds such as pyridine and quinoline; methanol, ethanol, propanol, 2-propanol, ethylene glycol, propylene glycol, Alcohols such as glycerin and water, and the like.
  • the solvents can be used alone or as a mixture of two or more. The amount of the solvent is usually about 1 ml to 100 ml with respect to the compound (I) lg.
  • organic base examples include pyridines such as pyridine, methylpyridine, ethylpyridine, dimethylpyridine, methylethylpyridine, getylviridine, pyridines such as trimethylpyridine, dimethylaminopyridine and 2,2-bipyridyl, triethylamine, tripropylamine and the like.
  • pyridines such as trimethylpyridine, dimethylaminopyridine and 2,2-bipyridyl, triethylamine, tripropylamine and the like.
  • trialkylamines such as tributylamine, N, N-dialkylanilines such as N, N-dimethylaniline and N, N-getylaniline, and liquid ammonia.
  • This reaction is carried out under cooling to room temperature, but is preferably carried out under heating.
  • the preferred reaction temperature is usually 30 to 250. More preferably, the temperature is from 80 to 200 ° C, and preferably from 110 to: L60 ° C.
  • the reaction time is usually several hours to several tens of hours.
  • This reaction may be carried out under atmospheric pressure, but is preferably carried out in a closed pressurized apparatus, and the internal pressure is usually 0.1 to 10 MPa, preferably 0.1 to 2 MPa, particularly It is preferably 0;; to 0.3 MPa.
  • R is various substituents as long as it is an electron-donating substituent which exhibits coordination to the above-mentioned catalyst, preferably a metal in the catalyst.
  • the atom bonded to the pyridine ring is a hetero atom that exhibits coordination to the metal in the catalyst.
  • the heteroatom is selected from atoms other than hydrogen or carbon, but is preferably N, 0, S, etc., more preferably N or 0, and particularly preferably N.
  • residue bonded to the hetero atom examples include hydrogen, alkyl, preferably C1 to C6 alkyl (eg, methyl, ethyl, n-propyl, t-butyl, etc.), lower alkylcarbonyl (eg, acetyl, Carbonyl) and the like.
  • alkyl preferably C1 to C6 alkyl (eg, methyl, ethyl, n-propyl, t-butyl, etc.)
  • lower alkylcarbonyl eg, acetyl, Carbonyl
  • R is preferably an optionally substituted amino (eg, amino, NHR 1 N (R 2 (R 1 is alkyl)) (eg, methylamino, ethylamino, dimethylamino, getylamino), lower alkylcarbonylamino (example: NHC OCH 3 )), optionally substituted hydroxy (eg, 0 H, OR 1 (eg, methoxy, ethoxy)) or optionally substituted thiol (eg, thiol, SR 1 (eg, Methylthio)) It is.
  • R is more preferably an optionally substituted amino, particularly preferably NH 2 . Since R is an electron donating group, naturally, for example, halogen, nitro, methyl halide and the like are excluded.
  • the compound (I) as a raw material is a known compound (eg, 3-amino-2-chloropyridin, 3-hydroxy-2-chloropyridine, 3-methoxy-2-chloropyridine) or a known compound containing these. It can be easily synthesized from compounds.
  • the compound (II) can be obtained by treating the reaction solution by a conventional method (concentration, extraction, separation, etc.). To obtain a higher quality compound (II), the second and third steps are preferably performed. (2nd step)
  • the second step is optionally performed when a copper catalyst is used in the reaction of the first step, and is a method of removing copper from the reaction mixture as copper sulfide.
  • the acid may be either an organic acid or an inorganic acid, but is preferably an inorganic acid, particularly preferably sulfuric acid.
  • concentration of sulfuric acid is about 10-80%, preferably 50-70%.
  • the amount of the acid used is, for example, about 1 ml to 10 ml for compound (I) 1 in the case of 64% sulfuric acid.
  • the temperature at which the acid is added is usually 0 to 50 ° C, preferably 0 to 25 ° C.
  • sulfide compounds such as sodium thiosulfate, sodium hydrosulfide, sodium sulfide, ammonium sulfide, potassium sulfide, lithium sulfide and hydrogen sulfide are added to the acidic mixture prepared above, and stirred for several hours to precipitate copper as copper sulfide. After that, the insoluble matter is filtered.
  • sodium thiosulfate sodium hydrosulfide and hydrogen sulfide are particularly preferred, and sodium thiosulfate is particularly preferred.
  • the amount of the sulfide compound used is, for example, about 1 ml to 15 ml for 1 g of the compound (1) in the case of a saturated aqueous solution of sodium thiosulfate.
  • the temperature at which the sulfide compound is added is usually 0 to 40 ° C, preferably 10 to 30 ° C.
  • the stirring time is usually 1 to 20 hours, depending on the state of copper sulfide precipitation.
  • Copper sulfide usually refers to monovalent and divalent copper sulfides, but may include metallic copper and sulfur.
  • the third step is a step of producing a salt of the compound (II) such as 2,3-diaminopyridine and a step of purifying the compound (II) using the salt.
  • a salt of the compound (II) such as 2,3-diaminopyridine
  • a step of purifying the compound (II) using the salt is described as an example.
  • the production of the salt of 2,3-diaminopyridine is preferably performed in the first step, More preferably, a base is added to the filtrate prepared in the second step to prepare a solution having a pH of preferably 8-9.
  • the base may be any of an organic base and an inorganic base, but is preferably an inorganic base, particularly preferably a 30 to 50% sodium hydroxide aqueous solution.
  • the base is used in an appropriate amount. For example, if the base is a 48% aqueous sodium hydroxide solution, add an appropriate amount until the solution has a pH of 8-9.
  • the temperature at which the base is added is usually 0 to 40 ° C.
  • This acid addition salt may be subjected to desalting treatment as described later to convert it to 2,3-diaminopyridine, and then to another salt.
  • the amount of the acid used is preferably 0.6 to 10 equivalents to 1 equivalent of the raw material 3-amino 2-chloropyridine. Particularly preferred is 0.8 to 1.4 equivalents.
  • crystals are precipitated in about 10 minutes to several tens of hours, preferably several hours, at room temperature with stirring. When no precipitation occurs, the crystals may be precipitated by, for example, applying a stimulus such as ultrasonic treatment and stirring under cooling or adding a seed crystal.
  • Salt binding has the advantage of good operability in the manufacturing process because of good filterability and easy separation from solvents (eg, water). Further, in a salt state at normal temperature and normal pressure, it is easy to obtain a stable and high quality product.
  • 2,3-Diaminopyridine can be obtained by treating the isolated and purified acid addition salt, preferably benzoate, with a base.
  • the base may be any of an inorganic base and an organic base, but is preferably an inorganic base.
  • the inorganic base include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate, and lithium carbonate. Particularly preferred is sodium hydroxide.
  • 2,3-Diaminopyridine can be obtained, for example, by suspending a salt of benzoic acid in water or an organic solvent, or in an organic solvent (eg, methanol, ethanol, chloroform, dichloromethan). After dissolving in ethyl acetate and ethyl acetate (preferably ethyl acetate), a base such as sodium hydroxide is added under cooling, and the mixture is stirred for several hours to produce.
  • a salt of benzoic acid in water or an organic solvent, or in an organic solvent (eg, methanol, ethanol, chloroform, dichloromethan).
  • an organic solvent eg, methanol, ethanol, chloroform, dichloromethan
  • a base such as sodium hydroxide
  • the amount of the solvent is usually about 1 ml to 100 ml per 1 g of the salt.
  • the amount of the base is preferably 1 to 10 equivalents to 1 equivalent of the salt.
  • the reaction temperature is generally 0 to 40 ° C, preferably 0 to 30 ° C.
  • the stirring time is usually 1 to several tens hours, preferably 1 to 2 hours.
  • 2,3-Diaminopyridine is obtained by treating a base-treated solution or a concentrated solution thereof with ethers (eg, dimethyl ether, diisopropyl ether, methyl tert-butyl ether), ethyl acetate, toluene, acetonitrile, and acetone.
  • ethers eg, dimethyl ether, diisopropyl ether, methyl tert-butyl ether
  • ethyl acetate ethyl acetate
  • toluene acetonitrile
  • acetone e.g, 2,3-Diaminopyridine
  • Organic or inorganic salts may precipitate, but can be removed by washing with a small amount of cold water.
  • the target crystal can be obtained more efficiently.
  • Compound (II) may be a solvate coordinated with any number of suitable organic solvents or water.
  • the compound ( ⁇ ⁇ ) produced in 43 can be further converted to various salts by standard methods. For example, it can be crystallized as a benzoate by treating with a hydrated solvent containing benzoic acid.
  • Examples of the salts of 2,3-diaminopyridine include salts with various bases and acid addition salts.
  • the aqueous ammonia in the above reaction mixture was distilled off under reduced pressure, and the residue was dissolved in a 64% aqueous sulfuric acid solution (4 ml).
  • a saturated aqueous sodium thiosulfate solution (3 ml) is added to the solution, and the mixture is stirred at room temperature for 2 hours.
  • the present invention relates to 2-amino-3-substituted pyridines such as 2,3-diaminopyridine and the like.
  • An industrially advantageous process for preparing the salts or solvates thereof is provided.
  • pharmaceuticals eg, CFM antibacterial agents
  • their raw materials can be industrially and efficiently produced.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne un processus de production de composé (II), qui se caractérise en ce qu'on fait réagir un composé (I) avec de l'ammoniac en présence d'un catalyseur. (I) (II). Dans ces formules, X est halogène et R est un substituant donneur d'électron possédant la propriété de se coordonner avec le catalyseur.
PCT/JP2004/000995 2003-02-06 2004-02-02 Processus de production de pyridine substitee 2-amino-3 WO2004069802A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2005504814A JPWO2004069802A1 (ja) 2003-02-06 2004-02-02 ２−アミノ−３−置換ピリジンの製造方法

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JP2003-029180 2003-02-06

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009022830A1 (de) 2008-10-24 2010-04-29 Jubilant Organosys Ltd. Verbessertes Verfahren zum Herstellen von Diaminopyridinen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49133377A (fr) * 1973-04-26 1974-12-21
JPS59122468A (ja) * 1982-12-28 1984-07-14 Toyo Soda Mfg Co Ltd ２−メトキシ−６−メチルアミノピリジンの製造法
JPS61221172A (ja) * 1985-03-23 1986-10-01 デグツサ・アクチエンゲゼルシヤフト ２‐アミノ‐３‐ニトロ‐６‐（４‐フルオロ‐ベンジルアミノ）‐ピリジンの製造法
JPH02139046A (ja) * 1988-11-18 1990-05-29 Daicel Chem Ind Ltd 遷移金属触媒の分離回収方法
JPH05339236A (ja) * 1992-06-05 1993-12-21 Nippon Synthetic Chem Ind Co Ltd:The ２，３−ジアミノピリジン類の製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49133377A (fr) * 1973-04-26 1974-12-21
JPS59122468A (ja) * 1982-12-28 1984-07-14 Toyo Soda Mfg Co Ltd ２−メトキシ−６−メチルアミノピリジンの製造法
JPS61221172A (ja) * 1985-03-23 1986-10-01 デグツサ・アクチエンゲゼルシヤフト ２‐アミノ‐３‐ニトロ‐６‐（４‐フルオロ‐ベンジルアミノ）‐ピリジンの製造法
JPH02139046A (ja) * 1988-11-18 1990-05-29 Daicel Chem Ind Ltd 遷移金属触媒の分離回収方法
JPH05339236A (ja) * 1992-06-05 1993-12-21 Nippon Synthetic Chem Ind Co Ltd:The ２，３−ジアミノピリジン類の製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CLARK-LEWIS J.W. ET AL: "Methylation of 3-aminopyridines and Preparation of 2-Amino-3-methylaminopyridine and 2:3-Diaminopyridine", J. CHEM. SOC., January 1957 (1957-01-01), pages 442 - 446, XP002979793 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009022830A1 (de) 2008-10-24 2010-04-29 Jubilant Organosys Ltd. Verbessertes Verfahren zum Herstellen von Diaminopyridinen
DE102009022830B4 (de) * 2008-10-24 2013-07-04 Jubilant Organosys Ltd. Verbessertes Verfahren zum Herstellen von Diaminopyridinen

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