JP2014514241A - 2−トリフルオロメチル−5−(1−置換)アルキルピリジンの調製のための改良された方法 - Google Patents
2−トリフルオロメチル−5−(1−置換)アルキルピリジンの調製のための改良された方法 Download PDFInfo
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- JP2014514241A JP2014514241A JP2013542059A JP2013542059A JP2014514241A JP 2014514241 A JP2014514241 A JP 2014514241A JP 2013542059 A JP2013542059 A JP 2013542059A JP 2013542059 A JP2013542059 A JP 2013542059A JP 2014514241 A JP2014514241 A JP 2014514241A
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- 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
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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
- C07D213/28—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
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- 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
Description
本願は、2010年12月3日出願の米国仮特許出願第61/419,279号の優先権を主張する。この仮出願の全内容は参照により本願に援用される。
〔式中、
R1及びR2は、独立にH、C1−C4アルキルを表すか、あるいはR1又はR2のいずれかはR3と一緒になって、4員〜6員の飽和環を表すか、あるいはR1はR2と一緒になって、O又はN原子で置換されていてもよい3員〜6員の飽和環を表し、
R3は、C1−C4アルキルを表すか、あるいはR3はR1又はR2のいずれかと一緒になって、4員〜6員の飽和環を表し、
Xは、CH2、O又はSを表す〕
の調製のための改良された方法に関し、
この方法において、
i)式(II)の4−アルコキシ−1,1,1−トリフルオロブト−3−エン−2−オン
〔式中、RはC1−C4アルキルを表す〕
が、エナミン(III)
〔式中、
R1、R2、R3及びXは、既に定義されたとおりであり、かつ
R4及びR5は、独立に、C1−C8アルキル、C2−C8アルケニル、C1−C8アリールアルキル、C1−C8ハロアルキル、C1−C8アルコキシアルキル、C1−C8アルキルアミノアルキル、アリール又はヘテロアリールであるか、あるいは、R4及びR5は、Nと一緒になって、5員又は6員の飽和又は不飽和環を表す〕
と縮合して、式(IV)の中間体
〔式中、R1、R2、R3、R4、R5及びXは、既に定義されたとおりである〕
が得られ、
ii)式(IV)の中間体が、アンモニア又はアンモニアを生成することのできる試薬の存在下で環化され、
改良点が、両方の工程を非極性溶媒中で縮合中間体IVの単離又は精製を行わずに実施することよりなる。
〔式中、
R1及びR2は、独立にH、C1−C4アルキルを表すか、あるいはR1又はR2のいずれかはR3と一緒になって、4員〜6員の飽和環を表すか、あるいはR1はR2と一緒になって、O又はN原子で置換されていてもよい3員〜6員の飽和環を表し、
R3は、C1−C4アルキルを表すか、あるいはR3はR1又はR2のいずれかと一緒になって、4員〜6員の飽和環を表し、かつ
Xは、CH2、O又はSを表す〕
は、式(II)の4−アルコキシ−1,1,1−トリフルオロブト−3−エン−2−オン:
〔式中、RはC1−C4アルキルを表す〕
を、エナミン(III)
〔式中、
R1、R2、R3及びXは、既に定義されたとおりであり、かつ
R4及びR5は、独立に、C1−C8アルキル、C2−C8アルケニル、C1−C8アリールアルキル、C1−C8ハロアルキル、C1−C8アルコキシアルキル、C1−C8アルキルアミノアルキル、アリール又はヘテロアリールであるか、あるいは、R4及びR5は、Nと一緒になって、5員又は6員の飽和又は不飽和環を表す〕
と縮合させて、式(IV)の中間体
〔式中、R1、R2、R3、R4、R5及びXは、既に定義されたとおりである〕を得ることにより、かつ、式(IV)の中間体をアンモニア又はアンモニアを生成することのできる試薬の存在下で環化させることにより調製される。この方法の改良点は、両方の工程を非極性溶媒中で縮合中間体IVの単離又は精製を行わずに実施することを含む。
〔式中、RはC1−C4アルキルを表す〕
をエナミン(III)
〔式中、R1、R2、R3、R4、R5及びXは、既に定義されたとおりである〕
と反応させて式(IV)の中間体
を得る。
製パドルを備えたオーバーヘッド機械式撹拌機、K熱電対を備えたガラス製サーモウェル、1,1,1−トリフルオロ−ブト−3−エン−2−オンの添加のためにProMinentポンプに接続されたテフロン(登録商標)製装入ライン(Teflon load line)及び窒素オイルバブラーを備えた還流冷却器を装備した500ミリリットル(mL)の3ツ口ジャケット付きガラス製反応器に添加した。トルエン(122.38g)を添加してエナミン濃度を23.2重量%に調節した。撹拌溶液を5℃未満まで冷却した。1,1,1−トリフルオロ−ブト−3−エン−2−オン(77.18g、純度97面積%、74.86g、0.445モル、1.09当量)を、ProMinentポンプへのラインを備えた、窒素を詰めた送出瓶に注入した。1,1,1−トリフルオロ−ブト−3−エン−2−オンを、ProMinent添加ポンプを介して36分かけて添加した。添加の間、温度は5℃を超えなかった。5℃未満で30分間撹拌を継続した。反応混合物を約25℃まで暖め、さらに5時間(h)撹拌した。かき混ぜを停止し、反応物を窒素下25℃で2日間(d)置いた。1,1,1−トリフルオロ−6−メチルチオ−5−(ピロリジン−1−イルメチレン)ヘプト−3−エン−2−オン生成物/トルエン溶液を反応器から排出し、反応器をトルエン(3×50mL)ですすぎ、排出した反応器の内容物に添加した。1,1,1−トリフルオロ−6−メチルチオ−5−(ピロリジン−1−イルメチレン)ヘプト−3−エン−2−オン生成物/トルエン溶液(251.06g)を、ピラジンを内部標準として用い、90秒(sec)のパルス遅延で1H−NMR分光法により分析すると、それはエナミンから収率79%で1,1,1−トリフルオロ−6−メチルチオ−5−(ピロリジン−1−イルメチレン)ヘプト−3−エン−2−オン生成物を示した。
実施例2:5−(1−(メチルチオ)エチル)−2−(トリフルオロメチル)ピリジンの調製
Claims (6)
- 2−トリフルオロメチル−5−(1−置換)−アルキルピリジン(I)
〔式中、
R1及びR2は、独立にH、C1−C4アルキルを表すか、あるいはR1又はR2のいずれかはR3と一緒になって、4員〜6員の飽和環を表すか、あるいはR1はR2と一緒になって、O又はN原子で置換されていてもよい3員〜6員の飽和環を表し、
R3は、C1−C4アルキルを表すか、あるいはR3はR1又はR2のいずれかと一緒になって、4員〜6員の飽和環を表し、かつ
Xは、CH2、O又はSを表す〕
の調製のための方法であって、
i)式(II)の4−アルコキシ−1,1,1−トリフルオロブト−3−エン−2−オン
〔式中、RはC1−C4アルキルを表す〕
を、エナミン(III)
〔式中、
R1、R2、R3及びXは、既に定義されたとおりであり、かつ
R4及びR5は、独立に、C1−C8アルキル、C2−C8アルケニル、C1−C8アリールアルキル、C1−C8ハロアルキル、C1−C8アルコキシアルキル、C1−C8アルキルアミノアルキル、アリール又はヘテロアリールであるか、あるいは、R4及びR5は、Nと一緒になって、5員又は6員の飽和又は不飽和環を表す〕と縮合させて、式(IV)の中間体
〔式中、
R1、R2、R3、R4、R5及びXは、既に定義されたとおりである〕を得る工程と、
ii)前記式(IV)の前記中間体を、アンモニア又はアンモニアを生成することのできる試薬の存在下で環化させる工程を含み、
改良点が、両方の工程を非極性溶媒中で前記縮合中間体IVの単離又は精製を行わずに実施することよりなる、方法。 - R1及びR2が、独立にH又はメチルを表し、R3がメチルを表し、XがSを表す、請求項1に記載の方法。
- 式(II)の前記分子が、約−20℃〜約35℃の温度でエナミン(III)と縮合される、請求項1に記載の方法。
- 式(II)の前記分子が、約−5℃〜約20℃の温度でエナミン(III)と縮合される、請求項1に記載の方法。
- 前記非極性溶媒がトルエンである、請求項1に記載の方法。
- 前記非極性溶媒がトルエンである、請求項2、3、又は4に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41927910P | 2010-12-03 | 2010-12-03 | |
US61/419,279 | 2010-12-03 | ||
PCT/US2011/061980 WO2012074857A2 (en) | 2010-12-03 | 2011-11-23 | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines |
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JP2014514241A true JP2014514241A (ja) | 2014-06-19 |
JP5828004B2 JP5828004B2 (ja) | 2015-12-02 |
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JP2013542059A Active JP5828004B2 (ja) | 2010-12-03 | 2011-11-23 | 2−トリフルオロメチル−5−(1−置換)アルキルピリジンの調製のための改良された方法 |
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US (1) | US8742125B2 (ja) |
EP (1) | EP2646416B9 (ja) |
JP (1) | JP5828004B2 (ja) |
KR (1) | KR20130124330A (ja) |
CN (1) | CN103814031B (ja) |
AR (1) | AR084099A1 (ja) |
AU (1) | AU2011336870B2 (ja) |
BR (1) | BR112013013290B1 (ja) |
CA (1) | CA2818513C (ja) |
CO (1) | CO6700894A2 (ja) |
IL (1) | IL226660A (ja) |
MX (1) | MX2013006190A (ja) |
PL (1) | PL2646416T3 (ja) |
RU (1) | RU2608317C2 (ja) |
UA (1) | UA113281C2 (ja) |
WO (1) | WO2012074857A2 (ja) |
ZA (1) | ZA201303872B (ja) |
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CN103814031B (zh) | 2010-12-03 | 2016-10-19 | 陶氏益农公司 | 制备2-三氟甲基-5-(1-取代的)烷基吡啶的改进方法 |
IN2014DN10677A (ja) * | 2012-06-30 | 2015-08-28 | Dow Agrosciences Llc | |
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 |
Citations (4)
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US20080033180A1 (en) * | 2006-08-07 | 2008-02-07 | Renga James M | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
WO2008030266A2 (en) * | 2006-09-01 | 2008-03-13 | Dow Agrosciences Llc | Insecticidal n-substituted (heteroaryl)alkyl sulfilmines |
US20090023782A1 (en) * | 2007-07-20 | 2009-01-22 | Dow Agrosciences Llc | Increasing plant vigor |
WO2010002577A1 (en) * | 2008-07-01 | 2010-01-07 | Dow Agrosciences Llc | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines |
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NO912475L (no) * | 1990-06-27 | 1991-12-30 | Sankyo Co | Tiazolidinkarboksylsyreamidderivater med antiallergisk aktivitet, og fremgangsmaate til fremstilling derav. |
RU2083562C1 (ru) * | 1993-02-05 | 1997-07-10 | Исихара Сангио Кайся Лтд. | Производные пиридина, способ их получения, инсектицидная композиция |
PT1254883E (pt) * | 1995-05-26 | 2009-10-02 | Ishihara Sangyo Kaisha | Processo para produção de 1,1,1-trifluoro-3-buten-2-onas substituídas |
CA2558647C (en) | 2004-04-08 | 2013-05-28 | Dow Agrosciences Llc | Insecticidal n-substituted sulfoximines |
TW201309635A (zh) | 2006-02-10 | 2013-03-01 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺(二) |
CN103814031B (zh) | 2010-12-03 | 2016-10-19 | 陶氏益农公司 | 制备2-三氟甲基-5-(1-取代的)烷基吡啶的改进方法 |
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- 2011-11-23 CN CN201180058142.8A patent/CN103814031B/zh active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US20080033180A1 (en) * | 2006-08-07 | 2008-02-07 | Renga James M | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
WO2008030266A2 (en) * | 2006-09-01 | 2008-03-13 | Dow Agrosciences Llc | Insecticidal n-substituted (heteroaryl)alkyl sulfilmines |
US20090023782A1 (en) * | 2007-07-20 | 2009-01-22 | Dow Agrosciences Llc | Increasing plant vigor |
WO2010002577A1 (en) * | 2008-07-01 | 2010-01-07 | Dow Agrosciences Llc | Improved process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines |
Also Published As
Publication number | Publication date |
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CA2818513A1 (en) | 2012-06-07 |
BR112013013290A2 (pt) | 2016-07-12 |
CN103814031A (zh) | 2014-05-21 |
MX2013006190A (es) | 2013-07-29 |
PL2646416T3 (pl) | 2017-03-31 |
KR20130124330A (ko) | 2013-11-13 |
RU2608317C2 (ru) | 2017-01-17 |
RU2013130244A (ru) | 2015-01-10 |
EP2646416A2 (en) | 2013-10-09 |
IL226660A (en) | 2017-05-29 |
JP5828004B2 (ja) | 2015-12-02 |
CA2818513C (en) | 2018-07-17 |
AU2011336870B2 (en) | 2016-03-03 |
US20120142933A1 (en) | 2012-06-07 |
WO2012074857A3 (en) | 2014-03-13 |
AU2011336870A1 (en) | 2013-05-30 |
WO2012074857A2 (en) | 2012-06-07 |
AR084099A1 (es) | 2013-04-17 |
CN103814031B (zh) | 2016-10-19 |
US8742125B2 (en) | 2014-06-03 |
EP2646416B9 (en) | 2016-12-21 |
CO6700894A2 (es) | 2013-06-28 |
EP2646416B1 (en) | 2016-09-07 |
ZA201303872B (en) | 2014-08-27 |
BR112013013290B1 (pt) | 2018-02-14 |
EP2646416A4 (en) | 2014-11-05 |
UA113281C2 (xx) | 2017-01-10 |
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