DK2867208T3 - PROCESS FOR THE PREPARATION OF 2,2-difluoroethylamine-derivatives by alkylation of 2,2-difluoroethylamine - Google Patents
PROCESS FOR THE PREPARATION OF 2,2-difluoroethylamine-derivatives by alkylation of 2,2-difluoroethylamine Download PDFInfo
- Publication number
- DK2867208T3 DK2867208T3 DK13730578.5T DK13730578T DK2867208T3 DK 2867208 T3 DK2867208 T3 DK 2867208T3 DK 13730578 T DK13730578 T DK 13730578T DK 2867208 T3 DK2867208 T3 DK 2867208T3
- Authority
- DK
- Denmark
- Prior art keywords
- difluoroethylamine
- chloro
- formula
- substituted
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- OVRWUZYZECPJOB-UHFFFAOYSA-N 2,2-difluoroethanamine Chemical compound NCC(F)F OVRWUZYZECPJOB-UHFFFAOYSA-N 0.000 title claims description 33
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000029936 alkylation Effects 0.000 title description 2
- 238000005804 alkylation reaction Methods 0.000 title description 2
- -1 2-chloro-pyrazin-5-yl Chemical group 0.000 claims description 55
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 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 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011084 recovery Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- 239000012868 active agrochemical ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- PYLCEKONTCTVEI-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)-n-(2,2-difluoroethyl)methanimine Chemical compound FC(F)CN=CC1=CC=C(Cl)N=C1 PYLCEKONTCTVEI-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
- SLLDUURXGMDOCY-UHFFFAOYSA-N 2-butyl-1h-imidazole Chemical compound CCCCC1=NC=CN1 SLLDUURXGMDOCY-UHFFFAOYSA-N 0.000 description 1
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 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
- 239000012071 phase Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07D213/60—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12174277 | 2012-06-29 | ||
| PCT/EP2013/063116 WO2014001245A1 (de) | 2012-06-29 | 2013-06-24 | Verfahren zur herstellung von 2,2-difluorethylamin-derivaten durch alkylierung von 2,2-difluorethylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2867208T3 true DK2867208T3 (en) | 2016-12-05 |
Family
ID=48670571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13730578.5T DK2867208T3 (en) | 2012-06-29 | 2013-06-24 | PROCESS FOR THE PREPARATION OF 2,2-difluoroethylamine-derivatives by alkylation of 2,2-difluoroethylamine |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9904676D0 (sv) * | 1999-12-20 | 1999-12-20 | Astra Ab | Novel compounds |
| DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| JP4821849B2 (ja) | 2006-04-10 | 2011-11-24 | 株式会社村田製作所 | 複合基板及び複合基板の製造方法 |
| DE102006033572A1 (de) * | 2006-07-20 | 2008-01-24 | Bayer Cropscience Ag | N'-Cyano-N-halogenalkyl-imidamid Derivate |
| EP2039684A1 (de) * | 2007-09-18 | 2009-03-25 | Bayer CropScience AG | Verfahren zur Herstellung von 2,2-Difluorethylamin-Derivaten durch Imin-Hydrierung |
| WO2009036900A1 (de) | 2007-09-18 | 2009-03-26 | Bayer Cropscience Ag | Verfahren zur herstellung von 2,2-difluorethylamin-derivaten durch amid-hydrierung |
| EP2230231A1 (de) * | 2009-03-16 | 2010-09-22 | Bayer CropScience AG | Verfahren zur Herstellung von 2,2-Difluorethylamin-Derivaten durch Imin-Hydrierung |
| KR101790159B1 (ko) * | 2010-06-15 | 2017-10-25 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 2,2-디플루오로-1-할로에탄의 알킬화에 의한 2,2-디플루오로에틸아민 유도체의 제조 방법 |
| ES2533307T3 (es) * | 2010-11-12 | 2015-04-09 | Bayer Intellectual Property Gmbh | Procedimiento de preparación de derivados de 2,2-difluoroetilamina partiendo de n (2,2 difluoroetil)prop-2-en-1 amina |
-
2013
- 2013-06-24 WO PCT/EP2013/063116 patent/WO2014001245A1/de active Application Filing
- 2013-06-24 ES ES13730578.5T patent/ES2603287T3/es active Active
- 2013-06-24 CN CN201380033732.4A patent/CN104379564B/zh active Active
- 2013-06-24 MX MX2014015622A patent/MX361289B/es active IP Right Grant
- 2013-06-24 BR BR112014032479-4A patent/BR112014032479B1/pt active IP Right Grant
- 2013-06-24 US US14/411,173 patent/US9376389B2/en active Active
- 2013-06-24 DK DK13730578.5T patent/DK2867208T3/en active
- 2013-06-24 EP EP13730578.5A patent/EP2867208B1/de active Active
- 2013-06-24 KR KR20147036103A patent/KR20150032537A/ko not_active Ceased
- 2013-06-24 IN IN10440DEN2014 patent/IN2014DN10440A/en unknown
- 2013-06-24 JP JP2015519021A patent/JP6175136B2/ja active Active
- 2013-06-28 TW TW102123118A patent/TWI593677B/zh not_active IP Right Cessation
-
2014
- 2014-12-15 IL IL236257A patent/IL236257A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP6175136B2 (ja) | 2017-08-02 |
| MX361289B (es) | 2018-12-03 |
| JP2015522574A (ja) | 2015-08-06 |
| US9376389B2 (en) | 2016-06-28 |
| KR20150032537A (ko) | 2015-03-26 |
| EP2867208B1 (de) | 2016-08-24 |
| BR112014032479A2 (pt) | 2017-06-27 |
| ES2603287T3 (es) | 2017-02-24 |
| CN104379564B (zh) | 2016-08-24 |
| IN2014DN10440A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-08-21 |
| WO2014001245A1 (de) | 2014-01-03 |
| TWI593677B (zh) | 2017-08-01 |
| IL236257A (en) | 2016-11-30 |
| MX2014015622A (es) | 2015-03-20 |
| US20150322011A1 (en) | 2015-11-12 |
| TW201408639A (zh) | 2014-03-01 |
| CN104379564A (zh) | 2015-02-25 |
| BR112014032479B1 (pt) | 2020-03-10 |
| IL236257A0 (en) | 2015-02-26 |
| EP2867208A1 (de) | 2015-05-06 |
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