JP2017507989A - 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 - Google Patents
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 Download PDFInfo
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- JP2017507989A JP2017507989A JP2016557945A JP2016557945A JP2017507989A JP 2017507989 A JP2017507989 A JP 2017507989A JP 2016557945 A JP2016557945 A JP 2016557945A JP 2016557945 A JP2016557945 A JP 2016557945A JP 2017507989 A JP2017507989 A JP 2017507989A
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- difluoroethylamine
- amine
- methyl
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- OVRWUZYZECPJOB-UHFFFAOYSA-N 2,2-difluoroethanamine Chemical compound NCC(F)F OVRWUZYZECPJOB-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 5
- 230000002152 alkylating effect Effects 0.000 title description 2
- QDQGMLOVCICKPV-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine Chemical compound FC(F)CNCC1=CC=C(Cl)N=C1 QDQGMLOVCICKPV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 150000007529 inorganic bases Chemical class 0.000 claims description 34
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000003444 phase transfer catalyst Substances 0.000 claims description 20
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
- 238000002474 experimental method Methods 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 6-chloropyridin-3-yl Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 230000002051 biphasic effect Effects 0.000 description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- FGJYOKRKWGBUKB-UHFFFAOYSA-N 1,2-difluoroethanamine Chemical class NC(F)CF FGJYOKRKWGBUKB-UHFFFAOYSA-N 0.000 description 1
- JWXMVJRAFLUMBC-UHFFFAOYSA-N 2-amino-2h-furan-5-one Chemical class NC1OC(=O)C=C1 JWXMVJRAFLUMBC-UHFFFAOYSA-N 0.000 description 1
- CMSOHDSVIRHPQB-UHFFFAOYSA-N 6-chloro-N-(3,3-difluoroprop-1-en-2-yl)pyridin-3-amine Chemical compound ClC1=CC=C(C=N1)NC(C(F)F)=C CMSOHDSVIRHPQB-UHFFFAOYSA-N 0.000 description 1
- AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GXDRBPSWEUQEDB-UHFFFAOYSA-N CC1NC(Cl)=CC=C1CNCC(F)F Chemical compound CC1NC(Cl)=CC=C1CNCC(F)F GXDRBPSWEUQEDB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000012868 active agrochemical ingredient Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- MEPLDDAONLVHEF-UHFFFAOYSA-M benzyl(triethyl)azanium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CC[N+](CC)(CC)CC1=CC=CC=C1 MEPLDDAONLVHEF-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- RGMABBBBPOTQIQ-UHFFFAOYSA-M hydrogen sulfate;tributyl(methyl)azanium Chemical compound OS([O-])(=O)=O.CCCC[N+](C)(CCCC)CCCC RGMABBBBPOTQIQ-UHFFFAOYSA-M 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- MWSPFHZPVVWJCO-UHFFFAOYSA-M hydron;methyl(trioctyl)azanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC MWSPFHZPVVWJCO-UHFFFAOYSA-M 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical group C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- QLPMKRZYJPNIRP-UHFFFAOYSA-M methyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC QLPMKRZYJPNIRP-UHFFFAOYSA-M 0.000 description 1
- OYGSUIIKXMDDNO-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroacetamide Chemical compound FC(F)C(=O)NCC1=CC=C(Cl)N=C1 OYGSUIIKXMDDNO-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- C07D213/24—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
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
実施例:
下記実施例を参照して、本発明についてさらに詳細に記述するが、本発明はそれら実施
例に限定されるものではない。
TBAB及び対応する塩基を使用して又は使用せずに実施された他の全ての例(例1−例5、例8−例15及び例17)は、例7と同様にして実施し、そして、TBABを用いた実験においては、DFEA、塩基及びTBABで構成される最初の反応混合物を55℃まで加熱した。
・ 当該反応は、ヒューニッヒ塩基の使用に伴う不利な点(工業的な大規模で得るのが困難である、後処理及び回収が困難であるなど)の全てを同時に回避することを可能とする無機塩基を用いて、良好な収率で実施することができる;
・ 当該反応は、無機塩基を用いて実施して、塩基としてトリエチルアミンを使用して達成される収率(例16及び例17:これらは、WO−A−2007/115644による)よりも明らかに高い収率を達成することができる;
・ 無機塩基としてアルカリ金属の水酸化物(NaOH、KOH)を使用することによって、別の無機塩基(Na2CO3)を使用して達成される収率よりも明らかに高い収率を達成することが可能となった; 無機塩基としてNaOH又はKOHを使用して達成される収率は、84.5%〜98.8%(例4、例6−例14)であったが、無機塩基としてNa2CO3を使用して達成される収率は、わずかに、72.4%〜82.5%の範囲内であった(例3、例5及び例15);
・ 最も高い収率は、無機塩基としてNaOHを用いて達成された(93.1%−98.8%);
・ 当該反応は、相関移動触媒(TBAB)の存在下及び非存在下の両方において、首尾よく実施される。
Claims (6)
- 前記無機塩基がNaOHである、請求項1に記載の調製方法。
- 前記反応を相関移動触媒の存在下で実施する、請求項1及び2のいずれかに記載の調製方法。
- 前記相関移動触媒が、有機アンモニウム塩又は有機ホスホニウム塩である、請求項3に記載の調製方法。
- 前記反応を相関移動触媒の非存在下で実施する、請求項1及び2のいずれかに記載の調製方法。
- 消費されなかった式(I)で表される2,2−ジフルオロエチルアミンをその反応後に留去し、次いで、前記調製方法に反応体として戻す、請求項1〜5のいずれかに記載の調製方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14161110.3 | 2014-03-21 | ||
EP14161110 | 2014-03-21 | ||
PCT/EP2015/055639 WO2015140198A1 (de) | 2014-03-21 | 2015-03-18 | Verfahren zur herstellung von n-[(6-chlorpyridin-3-yl)methyl]-2,2-difluorethan-1-amin durch alkylierung von 2,2-difluorethylamin |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017507989A true JP2017507989A (ja) | 2017-03-23 |
JP2017507989A5 JP2017507989A5 (ja) | 2018-04-26 |
JP6533233B2 JP6533233B2 (ja) | 2019-06-19 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2016557945A Active JP6533233B2 (ja) | 2014-03-21 | 2015-03-18 | 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 |
Country Status (12)
Country | Link |
---|---|
US (1) | US9890120B2 (ja) |
EP (1) | EP3119747B1 (ja) |
JP (1) | JP6533233B2 (ja) |
KR (1) | KR102360975B1 (ja) |
CN (1) | CN106103412B (ja) |
BR (1) | BR112016021564B1 (ja) |
DK (1) | DK3119747T3 (ja) |
ES (1) | ES2699927T3 (ja) |
IL (1) | IL247751B (ja) |
MX (1) | MX2016012057A (ja) |
TW (1) | TWI648263B (ja) |
WO (1) | WO2015140198A1 (ja) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009531348A (ja) * | 2006-03-31 | 2009-09-03 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換されたエナミノカルボニル化合物 |
CN103242225A (zh) * | 2012-02-13 | 2013-08-14 | 湖南化工研究院 | 吡啶甲胺基吡啶类化合物及其制备方法 |
WO2014001245A1 (de) * | 2012-06-29 | 2014-01-03 | Bayer Cropscience Ag | Verfahren zur herstellung von 2,2-difluorethylamin-derivaten durch alkylierung von 2,2-difluorethylamin |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006033572A1 (de) * | 2006-07-20 | 2008-01-24 | Bayer Cropscience Ag | N'-Cyano-N-halogenalkyl-imidamid Derivate |
KR101565391B1 (ko) | 2007-09-18 | 2015-11-03 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 아미드 수소화에 의한 2,2-디플루오로에틸아민 유도체의 제조방법 |
EP2039684A1 (de) | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zur Herstellung von 2,2-Difluorethylamin-Derivaten durch Imin-Hydrierung |
EP2039678A1 (de) * | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zum Herstellen von 4-Aminobut-2-enoliden |
EP2264008A1 (de) * | 2009-06-18 | 2010-12-22 | Bayer CropScience AG | Substituierte Enaminocarbonylverbindungen |
EP2582673B1 (de) | 2010-06-15 | 2014-08-06 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von 2,2-difluorethylamin-derivaten durch alkylierung mit 2,2- difluor-1-halogenethanen |
BR112013011707B1 (pt) * | 2010-11-12 | 2018-08-28 | Bayer Ip Gmbh | Processo para a preparação de derivados de 2,2- difluoroetilamina partindo de n-(2,2-difluoroetil) - prop - 2 - eno - 1 - amina |
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2015
- 2015-03-18 US US15/126,593 patent/US9890120B2/en active Active
- 2015-03-18 KR KR1020167029182A patent/KR102360975B1/ko active IP Right Grant
- 2015-03-18 DK DK15710775.6T patent/DK3119747T3/da active
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WO2014001245A1 (de) * | 2012-06-29 | 2014-01-03 | Bayer Cropscience Ag | Verfahren zur herstellung von 2,2-difluorethylamin-derivaten durch alkylierung von 2,2-difluorethylamin |
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BR112016021564B1 (pt) | 2021-03-23 |
CN106103412A (zh) | 2016-11-09 |
KR20160138158A (ko) | 2016-12-02 |
KR102360975B1 (ko) | 2022-02-08 |
EP3119747A1 (de) | 2017-01-25 |
TWI648263B (zh) | 2019-01-21 |
BR112016021564A2 (pt) | 2017-10-03 |
US9890120B2 (en) | 2018-02-13 |
JP6533233B2 (ja) | 2019-06-19 |
ES2699927T3 (es) | 2019-02-13 |
EP3119747B1 (de) | 2018-08-29 |
WO2015140198A1 (de) | 2015-09-24 |
MX2016012057A (es) | 2017-01-19 |
TW201623238A (zh) | 2016-07-01 |
IL247751B (en) | 2018-11-29 |
CN106103412B (zh) | 2019-03-19 |
US20170081284A1 (en) | 2017-03-23 |
DK3119747T3 (da) | 2019-01-02 |
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