DK2638010T3 - Fremgangsmåde til fremstilling af 2,2-difluorethylamin-derivater gående ud fra n-(2,2-difluorethyl)prop-2-en-1-amin - Google Patents

Fremgangsmåde til fremstilling af 2,2-difluorethylamin-derivater gående ud fra n-(2,2-difluorethyl)prop-2-en-1-amin Download PDF

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DK2638010T3
DK2638010T3 DK11782114.0T DK11782114T DK2638010T3 DK 2638010 T3 DK2638010 T3 DK 2638010T3 DK 11782114 T DK11782114 T DK 11782114T DK 2638010 T3 DK2638010 T3 DK 2638010T3
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pyrid
chloro
fluoro
methyl
formula
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DK11782114.0T
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Norbert Lui
Jens-Dietmar Heinrich
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Bayer Ip Gmbh
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/14—Preparation from compounds containing heterocyclic oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms

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

Claims (20)

1. En fremgangsmåde til fremstilling af 2,2-difluorethylaminderivater med formel (IV)
som omfatter de følgende trin (i) og (ii): trin (i): omsætning af N-(2,2-difluorethyl)prop-2-en-l-amin med formel (I)
med en forbindelse med formel (II) A-CH2-E (II) til en forbindelse med formel (III)
i givet fald i nærvær af en uorganisk eller organisk base, idet A i formlerne (II), (III) og (IV) står for pyrid-2-yl, pyrid-4-yl eller pyrid-3-yl, som i givet fald i 6. position kan være substitueret med fluor, chlor, brom, methyl, trifluormethyl eller trifluormethoxy, eller for 1,3-thiazol-5-yl, som i 2. position kan være substitueret med chlor eller methyl, eller for pyrid-3-yl med følgende formel
hvor X står for halogen, Ci-Ci2-alkyl eller Ci-Ci2-halogenalkyl, og Y står for halogen, Ci-Ci2-alkyl, Ci-Ci2-halogenalkyl, Ci-Ci2-halogenalkoxy, azido eller cyan, og E i formel (II) står for en fraspaltelig gruppe udvalgt blandt chlor, brom, rod, en aktiveret hydroxyforbindelse, mesylat, tosylat og S02CH3, og trin (ii): fjernelse af allylgruppen fra den i trin (i) opnåede forbindelse med formel (III), hvorved der opnås et difluorethylaminderivat med formel (IV) eller et salt heraf, i givet fald i nærvær af en katalysator og i givet fald i nærvær af en nukleofil.
2. Fremgangsmåde ifølge krav 1, idet trin (ii) gennemføres i nærvær af en katalysator, som indeholder et eller flere metaller fra grupperne 8 - 10 i det periodiske system, og i givet fald i nærvær af en nukleofil, idet nukleofilen er udvalgt blandt hydroxider, alkoholater, thiolater, carbanioner, halogenider, peroxider, cyanider og azider, thioler, sulfinsyrer, 2-mercaptobenzoesyre, malonsyre og derivater heraf og β-dicarbonylforbindelser, barbitursyrer, N,N'-dimethylbarbitursyre, aminer og ethanolamin.
3. Fremgangsmåde ifølge krav 2, idet katalysatoren er en palladium-katalysator.
4. Fremgangsmåde ifølge krav 3, idet katalysatoren er udvalgt blandt palladium(0)-katalysatorer, palladium-10% på kul, palladium (11)chlorid, palladium (II)acetat, bis(acetylacetonat)palladium(II), dichlorobis(triphenylphosphin)palladium(II), tetrakis(triethylphosphin)palladium og tetrakis(triphenylphosphin)palladium.
5. Fremgangsmåde ifølge et af kravene 1 til 4, idet den uorganiske base er udvalgt blandt hydrider, hydroxider, amider, alkoholater, acetater, fluorider, phosphater, carbonater og hydrogencarbonater af alkali- eller jordalkalimetaller, natriumamid, natriumhydrid, lithiumdiisopropylamid, natriummethanolat, kalium-tert- butanolat, natriumhydroxid, kaliumhydroxid, natriumacetat, natriumphosphat, kaliumphosphat, kaliumfluorid, caesiumfluorid, natriumcarbonat, kaliumcarbonat, kaliumhydrogencarbonat, natriumhydrogencarbonat og caesiumcarbonat, og den organiske base er udvalgt blandt aminer, substituerede eller usubstituerede pyridiner og substitueret eller usubstitueret triethylamin, trimethylamin, N, N-diisopropylethylamin, tri-n-propylamin, tri-n-butylamin, tri-n-hexylamin, tricyclohexylamin, N-methyl-cyclohexylamin, N-methylpyrrolidin, N-methylpiperidin, N-ethylpiperidin, N,N-dimethylanilin, N-methylmorpholin, pyridin, 2-, 3-, 4-picolin, 2-methyl-5-ethyl-pyridin, 2,6-lutidin, 2,4,6-collidin, 4-dimethylaminopyridin, quinolin, quinaldin, Ν,Ν,Ν,Ν- tetramethylethyldeniamin, N,N-dimethyl-1,4-diazacyclohexan, N, N-di-ethyl-1,4-diazacyclohexan, 1,8-bis- (dimethylamino)naphthalin, diazabicyclooctan (DABCO), diazabicyclononan (DBN), diazabicycloundecan (DBU), butylimidazol og methylimidazol.
6. Fremgangsmåde ifølge et af kravene 1 til 5, hvori E i formel (II) står for chlor, brom eller mesylat.
7. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 6-fluor-pyrid-3-yl, 6- chlor-pyrid-3-yl, 6-brom-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6- trifluormethyl-pyrid-3-yl, 6-trifluormethoxypyrid-3-yl, 2- chlor-1,3-thiazol-5-yl eller 2-methyl-l,3-thiazol-5-yl, 5,6-difluor-pyrid-3-yl, 5-chlor-6-fluor-pyrid-3-yl, 5-brom-6- fluor-pyrid-3-yl, 5-fluor-6-chlor-pyrid-3-yl, 5,6-dichlor- pyrid-3-yl, 5-brom-6-chlor-pyrid-3-yl, 5-fluor-6-brom-pyrid-3- yl, 5-chlor-6-brom-pyrid-3-yl, 5-methyl-6-fluor-pyrid-3-yl, 5- methyl-6-chlor-pyrid-3-yl, 5-methyl-6-brom-pyrid-3-yl, 5- difluormethyl-6-fluor-pyrid-3-yl eller 5-difluormethyl-6- chlor-pyrid-3-yl.
8. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 6-fluor-pyrid-3-yl, 6- chlor-pyrid-3-yl, 6-brompyrid-3-yl, 2-chlor-l,3-thiazol-5-yl, 5-fluor-6-chlor-pyrid-3-yl, 5,6-dichlor-pyrid-3-yl, 5-brom-6- chlor-pyrid-3-yl, 5-fluor-6-brom-pyrid-3-yl, 5-chlor-6-brom- pyrid-3-yl, 5,6-dibrom-pyrid-3-yl, 5-methyl-6-chlor-pyrid-3-yl eller 5-difluormethyl-6-chlor-pyrid-3-yl.
9. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 6-chlor-pyrid-3-yl.
10. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 6-brom-pyrid-3-yl.
11. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 2-chlor-l,3-thiazol-5-yl.
12. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 5-fluor-6-chlor-pyrid-3-yl.
13. Fremgangsmåde ifølge et af kravene 1 til 6, hvori A i formlerne (II), (III), og (IV) står for 5-fluor-6-brom-pyrid-3-yl.
14. En forbindelse med formel (III)
hvor A står for pyrid-2-yl, pyrid-4-yl eller pyrid-3-yl, som i givet fald i 6. position kan være substitueret med fluor, chlor, brom, methyl, trifluormethyl eller trifluormethoxy, eller for 1,3-thiazol-5-yl, som i 2. position kan være substitueret med chlor eller methyl, eller for pyrid-3-yl med følgende formel
hvor X står for halogen, Ci-Ci2_alkyl eller Ci-Ci2-halogenalkyl, og Y står for halogen, Ci-Ci2-alkyl, Ci-Ci2-halogenalkyl, Ci-Ci2-halogenalkoxy, azido eller cyan.
15. Forbindelse med formel (III) ifølge krav 14, hvori A står for 6-fluor-pyrid-3-yl, 6-chlor-pyrid-3-yl, 6-brom-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluormethyl-pyrid-3-yl, 6- trifluormethoxypyrid-3-yl, 2-chlor-l,3-thiazol-5-yl eller 2- methyl-1,3-thiazol-5-yl, 5,6-difluor-pyrid-3-yl, 5-chlor-6-fluor-pyrid-3-yl, 5-brom-6-fluor-pyrid-3-yl, 5-fluor-6-chlor- pyrid-3-yl, 5,6-dichlor-pyrid-3-yl, 5-brom-6-chlor-pyrid-3-yl, 5-fluor-6-brom-pyrid-3-yl, 5-chlor-6-brom-pyrid-3-yl, 5- methyl-6-fluor-pyrid-3-yl, 5-methyl-6-chlor-pyrid-3-yl, 5- methyl-6-brom-pyrid-3-yl, 5-difluormethyl-6-fluor-pyrid-3-yl eller 5-difluormethyl-6-chlor-pyrid-3-yl.
16. Forbindelse med formel (III) ifølge krav 14, hvori A står for 6-chlor-pyrid-3-yl.
17. Forbindelse med formel (III) ifølge krav 14, hvori A står for 6-brom-pyrid-3-yl.
18. Forbindelse med formel (III) ifølge krav 14, hvori A står for 2-chlor-l,3-thiazol-5-yl.
19. Forbindelse med formel (III) ifølge krav 14, hvori A står for 5-fluor-6-chlor-pyrid-3-yl.
20. Forbindelse med formel (III) ifølge krav 14, hvori A står for 5-fluor-6-brom-pyrid-3-yl.
DK11782114.0T 2010-11-12 2011-11-08 Fremgangsmåde til fremstilling af 2,2-difluorethylamin-derivater gående ud fra n-(2,2-difluorethyl)prop-2-en-1-amin DK2638010T3 (da)

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US41300810P 2010-11-12 2010-11-12
EP10191066 2010-11-12
PCT/EP2011/069625 WO2012062740A1 (de) 2010-11-12 2011-11-08 Verfahren zur herstellung von 2,2-difluorethylamin-derivaten ausgehend von n-(2,2-difluorethyl)prop-2-en-1-amin

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US (1) US8586756B2 (da)
EP (1) EP2638010B1 (da)
JP (1) JP5845276B2 (da)
KR (1) KR101837072B1 (da)
CN (1) CN103313969A (da)
BR (1) BR112013011707B1 (da)
DK (1) DK2638010T3 (da)
ES (1) ES2533307T3 (da)
IL (1) IL226194A (da)
MX (1) MX2013004968A (da)
TW (1) TWI515180B (da)
WO (1) WO2012062740A1 (da)

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CN104379564B (zh) * 2012-06-29 2016-08-24 拜耳农作物科学股份公司 通过2,2-二氟乙胺的烷基化制备2,2-二氟乙胺衍生物的方法
JP6533233B2 (ja) * 2014-03-21 2019-06-19 バイエル・クロップサイエンス・アクチェンゲゼルシャフト ２，２−ジフルオロエチルアミンをアルキル化することによりｎ−［（６−クロロピリジノ−３−イル）メチル］−２，２−ジフルオロエタン−１−アミンを調製する方法
CN108383848A (zh) * 2018-03-27 2018-08-10 石家庄蒎格医药科技有限公司 聚乙二醇纳洛酮新杂质及其制备方法

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IL226194A (en) 2015-04-30
IL226194A0 (en) 2013-07-31
ES2533307T3 (es) 2015-04-09
EP2638010B1 (de) 2014-12-31
JP2014501711A (ja) 2014-01-23
CN103313969A (zh) 2013-09-18
TWI515180B (zh) 2016-01-01
US20120123130A1 (en) 2012-05-17
WO2012062740A1 (de) 2012-05-18
KR20130101112A (ko) 2013-09-12
BR112013011707A2 (pt) 2016-07-12
US8586756B2 (en) 2013-11-19
KR101837072B1 (ko) 2018-03-09
MX2013004968A (es) 2013-06-07
BR112013011707B1 (pt) 2018-08-28
TW201307286A (zh) 2013-02-16
JP5845276B2 (ja) 2016-01-20
EP2638010A1 (de) 2013-09-18

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