AR084099A1 - Procedimiento mejorado para la preparacion de 2-trifluorometil-5-(1-substituido)-alquilpiridinas - Google Patents
Procedimiento mejorado para la preparacion de 2-trifluorometil-5-(1-substituido)-alquilpiridinasInfo
- Publication number
- AR084099A1 AR084099A1 ARP110104520A ARP110104520A AR084099A1 AR 084099 A1 AR084099 A1 AR 084099A1 AR P110104520 A ARP110104520 A AR P110104520A AR P110104520 A ARP110104520 A AR P110104520A AR 084099 A1 AR084099 A1 AR 084099A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- alkyl
- taken together
- members
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000002081 enamines Chemical class 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- 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
- C07D213/08—Preparation by ring-closure
-
- 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
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Reivindicación 1: Un procedimiento para la preparación de 2-trifluorometil-5-(1-sustituido)-alquilpiridina de fórmula (1), en donde R1 y R2 independientemente representan H, alquilo C1-4, o cualquiera entre R1 o R2 tomados conjuntamente con R3 representan un anillo saturado de 4 a 6 miembros, o R1 tomado conjuntamente con R2 representa un anillo saturado de 3 a 6 miembros opcionalmente sustituido con un átomo O ó N; R3 representa alquilo C1-4 o R3 tomados conjuntamente con R1 o R2 representan un anillo saturado de 4 a 6 miembros; y X representa CH2, O ó S, en donde: i) un 4-alcoxi-1,1,1-trifluorobut-3-en-2-ona de la fórmula (2) en donde R representa a alquilo C1-4 es condensado con una enamina de fórmula (3) en donde R1, R2, R3 y X son tal como se definen previamente, y R4 y R5 independientemente representan alquilo C1-8, alquenilo C2-8, arilalquilo C1-8, haloalquilo C1-8, alcoxialquilo C1-8, alquilaminoalquilo C1-8, arilo o heteroarilo o R4 y R5 tomados conjuntamente con N representan un anillo saturado o insaturado de 5 ó 6 miembros, para proveer un intermedio de la fórmula (4) en donde R1, R2, R3, R4, R5 y X son tal como se definen previamente, y ii) el intermedio de la fórmula (4) es ciclizado en presencia de amoníaco o un reactivo capaz de generar amoníaco, en donde la mejora comprende llevar a cabo los dos pasos en un solvente no polar sin aislamiento o purificación del intermedio de condensación de fórmula (4).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41927910P | 2010-12-03 | 2010-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR084099A1 true AR084099A1 (es) | 2013-04-17 |
Family
ID=46162833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110104520A AR084099A1 (es) | 2010-12-03 | 2011-12-02 | Procedimiento mejorado para la preparacion de 2-trifluorometil-5-(1-substituido)-alquilpiridinas |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8742125B2 (es) |
| EP (1) | EP2646416B9 (es) |
| JP (1) | JP5828004B2 (es) |
| KR (1) | KR20130124330A (es) |
| CN (1) | CN103814031B (es) |
| AR (1) | AR084099A1 (es) |
| AU (1) | AU2011336870B2 (es) |
| BR (1) | BR112013013290B1 (es) |
| CA (1) | CA2818513C (es) |
| CO (1) | CO6700894A2 (es) |
| IL (1) | IL226660A (es) |
| MX (1) | MX2013006190A (es) |
| PL (1) | PL2646416T3 (es) |
| RU (1) | RU2608317C2 (es) |
| UA (1) | UA113281C2 (es) |
| WO (1) | WO2012074857A2 (es) |
| ZA (1) | ZA201303872B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130124330A (ko) | 2010-12-03 | 2013-11-13 | 다우 아그로사이언시즈 엘엘씨 | 2-트리플루오로메틸-5-(1-치환)알킬피리딘의 개선된 제조 방법 |
| JP6242392B2 (ja) * | 2012-06-30 | 2017-12-06 | ダウ アグロサイエンシィズ エルエルシー | ピリジンｎ−オキシドおよびそれらの製法 |
| CN102977005A (zh) * | 2012-11-08 | 2013-03-20 | 安徽国星生物化学有限公司 | 2，3，5-三甲基吡啶的提纯方法 |
| CN116535391B (zh) * | 2023-05-05 | 2025-04-25 | 南京林业大学 | 一种2-烷基吡啶类手性化合物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA914888B (en) * | 1990-06-27 | 1992-04-29 | Sankyo Co | Thiazolidinecarboxylic acid amide derivatives having antiallergic activity,their preparation and their use |
| RU2083562C1 (ru) * | 1993-02-05 | 1997-07-10 | Исихара Сангио Кайся Лтд. | Производные пиридина, способ их получения, инсектицидная композиция |
| ATE443693T1 (de) * | 1995-05-26 | 2009-10-15 | Ishihara Sangyo Kaisha | Verfahren zur herstellung substituierter 1,1,1- trifluoro-3-buten-2-one |
| MXPA06011589A (es) | 2004-04-08 | 2006-12-20 | Dow Agrosciences Llc | Sulfoximinas n-sustituidas insecticidas. |
| TWI398433B (zh) | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺 |
| TWI383973B (zh) | 2006-08-07 | 2013-02-01 | Dow Agrosciences Llc | 用於製備２-取代-５-（１-烷硫基）烷基吡啶之方法 |
| TWI387585B (zh) * | 2006-09-01 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之ｎ-取代（雜芳基）烷基烴基硫亞胺 |
| KR101512528B1 (ko) * | 2007-07-20 | 2015-04-15 | 다우 아그로사이언시즈 엘엘씨 | 식물 생장력의 증가 |
| MX2011000196A (es) * | 2008-07-01 | 2011-03-24 | Dow Agrosciences Llc | Proceso mejorado para la preparacion de alquilpiridinas 2-trifluorometil-5-(1-sustituidas). |
| KR20130124330A (ko) | 2010-12-03 | 2013-11-13 | 다우 아그로사이언시즈 엘엘씨 | 2-트리플루오로메틸-5-(1-치환)알킬피리딘의 개선된 제조 방법 |
-
2011
- 2011-11-23 KR KR1020137014014A patent/KR20130124330A/ko not_active Ceased
- 2011-11-23 US US13/303,182 patent/US8742125B2/en active Active
- 2011-11-23 CA CA2818513A patent/CA2818513C/en active Active
- 2011-11-23 MX MX2013006190A patent/MX2013006190A/es active IP Right Grant
- 2011-11-23 EP EP11844184.9A patent/EP2646416B9/en active Active
- 2011-11-23 AU AU2011336870A patent/AU2011336870B2/en active Active
- 2011-11-23 JP JP2013542059A patent/JP5828004B2/ja active Active
- 2011-11-23 RU RU2013130244A patent/RU2608317C2/ru active
- 2011-11-23 CN CN201180058142.8A patent/CN103814031B/zh active Active
- 2011-11-23 PL PL11844184T patent/PL2646416T3/pl unknown
- 2011-11-23 WO PCT/US2011/061980 patent/WO2012074857A2/en not_active Ceased
- 2011-11-23 BR BR112013013290-6A patent/BR112013013290B1/pt active IP Right Grant
- 2011-11-23 UA UAA201308355A patent/UA113281C2/uk unknown
- 2011-12-02 AR ARP110104520A patent/AR084099A1/es active IP Right Grant
-
2013
- 2013-05-28 ZA ZA2013/03872A patent/ZA201303872B/en unknown
- 2013-05-29 CO CO13131752A patent/CO6700894A2/es unknown
- 2013-05-30 IL IL226660A patent/IL226660A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| UA113281C2 (xx) | 2017-01-10 |
| JP2014514241A (ja) | 2014-06-19 |
| CN103814031A (zh) | 2014-05-21 |
| EP2646416A4 (en) | 2014-11-05 |
| EP2646416B9 (en) | 2016-12-21 |
| JP5828004B2 (ja) | 2015-12-02 |
| RU2013130244A (ru) | 2015-01-10 |
| CN103814031B (zh) | 2016-10-19 |
| WO2012074857A3 (en) | 2014-03-13 |
| MX2013006190A (es) | 2013-07-29 |
| KR20130124330A (ko) | 2013-11-13 |
| CA2818513C (en) | 2018-07-17 |
| BR112013013290A2 (pt) | 2016-07-12 |
| EP2646416B1 (en) | 2016-09-07 |
| AU2011336870B2 (en) | 2016-03-03 |
| WO2012074857A2 (en) | 2012-06-07 |
| IL226660A (en) | 2017-05-29 |
| AU2011336870A1 (en) | 2013-05-30 |
| CA2818513A1 (en) | 2012-06-07 |
| BR112013013290B1 (pt) | 2018-02-14 |
| PL2646416T3 (pl) | 2017-03-31 |
| RU2608317C2 (ru) | 2017-01-17 |
| ZA201303872B (en) | 2014-08-27 |
| US20120142933A1 (en) | 2012-06-07 |
| EP2646416A2 (en) | 2013-10-09 |
| CO6700894A2 (es) | 2013-06-28 |
| US8742125B2 (en) | 2014-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |