EP0631579A1 - Process and intermediates for the preparation of substituted d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo 1,5-a]pyridine-1,3-diones - Google Patents

Process and intermediates for the preparation of substituted d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo 1,5-a]pyridine-1,3-diones

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Publication number
EP0631579A1
EP0631579A1 EP93906536A EP93906536A EP0631579A1 EP 0631579 A1 EP0631579 A1 EP 0631579A1 EP 93906536 A EP93906536 A EP 93906536A EP 93906536 A EP93906536 A EP 93906536A EP 0631579 A1 EP0631579 A1 EP 0631579A1
Authority
EP
European Patent Office
Prior art keywords
general formula
hydrogen
optionally
acid
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP93906536A
Other languages
German (de)
English (en)
French (fr)
Inventor
Michael Ganzer
Reinhold Puttner
Hartmut Seba
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
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 Schering AG filed Critical Schering AG
Publication of EP0631579A1 publication Critical patent/EP0631579A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring

Definitions

  • This invention relates to a process and intermediates for the preparation of substituted D,L-2-(7-fluoro- 3,4-dihydro-3-oxo-2H-l,4-benzoxazin-6-yl)perhydro- imidazo[l,5-a]pyridine-l,3-diones of general formula I
  • R 1 is C ⁇ Cg-al yl, C 2 -C 6 -alkenyl or C 3 -C 6 -alkynyl.
  • the compounds of formula I have herbicidal activity against a broad spectrum of monocotyledonous and dicotyledonous weeds in agricultural crops. Their preparation and use are described in EP 311 135.
  • 6-amino-2H-l,4-benzoxazin-3 (4H)-one is not very soluble in a number of solvents, so that the compound, which is obtained by an environmentally damaging catalytic hydrogenation, can be separated from the catalyst only under great difficulty.
  • This process has the further disadvantage that the synthesis goes via an isocyanate intermediate, whose preparation on the one hand involves phosgene or triphosgene and on the other hand the presence of further reactive groups in the molecule is only very limited.
  • This has the consequence that the introduction of the sometimes very expensive group R 1 must be introduced before the isocyanate step which make the preparation of the end product considerably more expensive. From the industrial viewpoint this process is therefore not particularly suitable for a large scale production.
  • the object of the present invention is to provide a new process which allows preparation of compounds of general formula I without any problems on an industrial scale, and under mild reaction conditions, whilst avoiding the stated disadvantages.
  • acetyl chloride or acetic anhydride is reacted with acetyl chloride or acetic anhydride, in the presence of an acid binding agent, optionally in a suitable solvent.
  • R 4 is hydrogen or C 1 -C 4 -alkyl and Y is halogen, methanesulfonyloxy or p-toluenesulfonyloxy,
  • phenoxyacetic acid, so formed, of general formula V is nitrated with nitric acid, or an organic or inorganic derivative thereof, optionally in a suitable solvent,
  • H is hydrogenated with hydrogen, in the presence of a suitable catalyst in an inert solvent, or reduced with a chemical reducing agent in the presence of an inert solvent,
  • X is halogen, nitro or cyano and n is an integer of 0 to 5, in a suitable inert solvent, optionally with the addition of an organic or inorganic acid binding agent,
  • R 2 is hydrogen, methyl or ethyl, in an inert solvent, optionally with the addition of an organic or inorganic acid binding agent,
  • R- - XIII in which R 1 has the meaning given in formula I and W is chlorine, bromine, iodine, p-toluenesulfonyloxy or methanesulfonyloxy, optionally with the addition of a base in a suitable solvent.
  • Process step a) is generally carried out by reacting the starting materials with or without a solvent, optionally with the addition of an inorganic or organic base at a temperature between 0 and 150°C.
  • the reaction also can optionally be carried out in a two phase mixture, for example water-methyl isobutyl ketone.
  • Suitable bases are alkali and alkaline earth metal hydroxides, carbonates and/or hydrogen carbonates, tertiary aliphatic amines, as well as heterocyclic bases. Examples include sodium and potassium hydroxide, sodium and potassium carbonate, sodium and potassium hydrogen carbonate, triethyla ine and pyridine.
  • Suitable solvents include hydrocarbons, such as toluene, chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, alcohols such as methanol or ethanol, ketones, such as acetone, butanone or methyl isobutyl ketone, and nitriles, such as acetonitrile, and also two phase mixtures with water.
  • hydrocarbons such as toluene
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether or tetrahydrofuran
  • alcohols such as methanol or ethanol
  • ketones such as acetone, butanone or methyl isobutyl ketone
  • nitriles such as acetonitrile
  • Process step b) is generally carried out by reacting the starting materials in an inert solvent, optionally with the addition of an inorganic or organic base at a temperature between 0 and 150°C, preferably at the boiling point of the solvent.
  • Suitable bases are alkali and alkaline earth metal hydroxides, carbonates and/or hydrogen carbonates, tertiary aliphatic amines, as well as heterocyclic bases. Examples include sodium and potassium hydroxide, sodium and potassium carbonate, sodium and potassium hydrogen carbonate, triethylamine and pyridine.
  • Suitable solvents include water, hydrocarbons such as toluene, chlorinated hydrocarbons such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, alcohols such as methanol, ethanol or isopropanol, ketones, such as acetone, butanone or methyl isobutyl ketone, and nitriles, such as acetonitrile.
  • hydrocarbons such as toluene
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether or tetrahydrofuran
  • alcohols such as methanol, ethanol or isopropanol
  • ketones such as acetone, butanone or methyl isobutyl ketone
  • Two phase mixtures with water and a water immiscible organic solvent can be used with the addition of a phase transfer catalyst.
  • Process step c) can generally be carried out according to known processes for nitration of phenyl ethers, as described for example in Houben- eyl, Vol. X/l, page 566 ff. Nitration of the aro atics in sulfuric acid solution by adding sulfuric acid/nitric acid mixtures with cooling has been proved.
  • Process stage d) is generally carried out according to known processes for reduction of an aromatic nitro group, for example as described in Houben-Weyl, Vol. XI/1, page 360 ff.
  • Hydrogenation with hydrogen in a suitable solvent in the presence of catalyst is particularly preferred.
  • Suitable solvents include water, hydrocarbons, such as toluene, xylene or hexane, chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran, alcohols, such as methanol, ethanol or isopropanol, esters such as ethyl acetate, or also carboxamides, such as dimethylformamide.
  • hydrocarbons such as toluene, xylene or hexane
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran
  • alcohols such as methanol, ethanol or isopropanol
  • esters such as ethyl acetate
  • carboxamides such as dimethyl
  • catalysts there can be used known hydrogenation catalysts. Examples are Raney-nickel, palladium or platinum oxide.
  • the process can be carried out over a wide temperature range from 0 to 150°C, preferably from 20°C to 100°C.
  • the reaction can be carried out under normal pressure but higher pressures can be used.
  • the reduction may also be under liquid conditions, for example, using iron powder in dilute acetic acid in the presence of glacial acetic acid and ethyl acetate.
  • the resulting 2-(2-acetamido-4-amino-5-fluoro- phenoxy)acetic acid derivatives are new.
  • Process step e) is generally carried out by reacting the starting materials in a suitable solvent, optionally with the addition of an inorganic or organic base at a temperature between 0 and 50°C.
  • the reaction can also optionally be carried out in a two phase mixture with water and a water immiscible organic solvent optionally with the addition of a phase transfer catalyst.
  • Suitable bases are alkali and alkaline earth metal hydroxides, carbonates and/or hydrogen carbonates, tertiary aliphatic amines as well as heterocyclic bases. Examples include sodium and potassium hydroxide, sodium and potassium hydrogen carbonate, calcium carbonate, magnesium oxide, triethylamine and pyridine.
  • Suitable solvents include hydrocarbons such as toluene, chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, and ketones, such as acetone, butanone or methyl isobutyl ketone.
  • hydrocarbons such as toluene
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether or tetrahydrofuran
  • ketones such as acetone, butanone or methyl isobutyl ketone.
  • Process step f) is generally carried out by reacting the starting materials in a suitable solvent, at a temperature between 20 and 130°C, optionally with the addition of an inorganic or organic base.
  • the reaction time is from 0.5 to 10 hours.
  • Suitable bases are alkali and alkaline earth metal hydroxides, carbonates and/or hydrogen carbonates, tertiary aliphatic and aromatic amines as well as heterocyclic bases. Examples include sodium and potassium hydroxide, potassium tert.-butanolate, sodium and potassium hydrogen carbonate, triethylamine and pyridine.
  • Suitable solvents include hydrocarbons such as toluene, chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, ketones, such as acetone, butanone or methyl isobutyl ketone and nitriles, such as acetonitrile.
  • hydrocarbons such as toluene
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether or tetrahydrofuran
  • ketones such as acetone, butanone or methyl isobutyl ketone
  • nitriles such as acetonitrile.
  • hydantoin can be formed from ⁇ -aminocarboxylic acid esters and isocyanates, see for example EP 0 272 594.
  • the disadvantage is -that the preparation of the corresponding isocyanate involves phosgene or triphosgene. Further in the known processes the presence of further reactive groups in the molecule is not possible since the corresponding isocyanate cannot be prepared.
  • the process of the invention allows the preparation of hydantoins with further functional groups, as contained in compounds of general formula XI, where also the use of phosgene or triphosgene can be avoided.
  • Process step g) is generally carried out by reacting the starting materials in a suitable inert solvent, optionally with the addition of an inorganic or organic acid at a temperature between 20 and 150°C, preferably at the boiling point of the solvent. It can also however be carried out in the absence of additional solvent, in a process in which for example, the starting materials are dissolved directly in the appropriate acid or their mixtures.
  • inorganic acids are hydrochloric acid and sulfuric acid and of organic acids are acetic acid or p-toluenesulfonic acid.
  • Suitable solvents include hydrocarbons such as hexane, cyclohexane, toluene or xylene, and chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane.
  • Process step h) is generally carried out by reacting the starting materials in a suitable solvent, optionally with the addition of an inorganic or organic base at a temperature between -10 and 150°C.
  • the reaction can also be carried out in a two phase system with water using a phase transfer catalyst.
  • Suitable bases are alkali and alkaline earth metal hydroxides, carbonates and/or hydrogen carbonates, tertiary aliphatic amines as well as heterocyclic bases. Examples include sodium and potassium hydroxide, sodium and potassium hydrogen carbonate, sodium hydride, triethylamine and pyridine.
  • Suitable solvents include hydrocarbons such as toluene, chlorinated hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, ketones, such as acetone, butanone or methyl isobutyl ketone, carboxamides, such as dimethylformamide and nitriles, such as acetonitrile.
  • hydrocarbons such as toluene
  • chlorinated hydrocarbons such as methylene chloride or chloroform
  • ethers such as diethyl ether or tetrahydrofuran
  • ketones such as acetone, butanone or methyl isobutyl ketone
  • carboxamides such as dimethylformamide
  • nitriles such as acetonitrile.
  • the compounds of general formulae I, XI and XII are optically active.
  • the compounds can optionally be present as pure enantiomers or as their mixtures.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP93906536A 1992-03-17 1993-03-10 Process and intermediates for the preparation of substituted d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo 1,5-a]pyridine-1,3-diones Withdrawn EP0631579A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4208778A DE4208778C1 (enrdf_load_stackoverflow) 1992-03-17 1992-03-17
DE4208778 1992-03-17
PCT/EP1993/000598 WO1993019065A1 (en) 1992-03-17 1993-03-10 Process and intermediates for the preparation of substituted d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo[1,5-a]pyridine-1,3-diones

Publications (1)

Publication Number Publication Date
EP0631579A1 true EP0631579A1 (en) 1995-01-04

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Family Applications (1)

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EP93906536A Withdrawn EP0631579A1 (en) 1992-03-17 1993-03-10 Process and intermediates for the preparation of substituted d,l-2-(7-fluoro-3,4-dihydro-3-oxo-2h-1,4-benzoxazin-6-yl)-perhydroimidazo 1,5-a]pyridine-1,3-diones

Country Status (7)

Country Link
EP (1) EP0631579A1 (enrdf_load_stackoverflow)
JP (1) JPH07504671A (enrdf_load_stackoverflow)
DE (1) DE4208778C1 (enrdf_load_stackoverflow)
HU (1) HU211068B (enrdf_load_stackoverflow)
IL (1) IL104810A0 (enrdf_load_stackoverflow)
TW (1) TW213915B (enrdf_load_stackoverflow)
WO (1) WO1993019065A1 (enrdf_load_stackoverflow)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1280266C (zh) * 2000-06-09 2006-10-18 萨诺费－阿文蒂斯德国有限公司 酰基苯基脲衍生物,其制备方法和作为药物的用途
JP2013540113A (ja) 2010-10-01 2013-10-31 ビーエーエスエフ ソシエタス・ヨーロピア 除草性ベンゾオキサジノン

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3734745A1 (de) * 1987-10-09 1989-04-20 Schering Ag Tetrahydropyrrolo(2,1-c)(1,2,4)-thiadiazol-3-ylideniminobenzoxazinone und andere heterocyclisch substituierte azole und azine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9319065A1 *

Also Published As

Publication number Publication date
WO1993019065A1 (en) 1993-09-30
JPH07504671A (ja) 1995-05-25
HUT68172A (en) 1995-05-29
HU211068B (en) 1995-10-30
DE4208778C1 (enrdf_load_stackoverflow) 1993-09-23
IL104810A0 (en) 1993-06-10
TW213915B (enrdf_load_stackoverflow) 1993-10-01
HU9402674D0 (en) 1994-12-28

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Free format text: PROCESS AND INTERMEDIATES FOR THE PREPARATION OF SUBSTITUTED D,L-2-(7-FLUORO-3,4-DIHYDRO-3-OXO-2H-1,4-BENZOXAZIN-6-YL)-PERHYDROIMIDAZO 1,5-A PYRIDINE-1,3-DIONES