JP2013530984A - 4−ヒドロキシピリジン類の製造方法 - Google Patents
4−ヒドロキシピリジン類の製造方法 Download PDFInfo
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- JP2013530984A JP2013530984A JP2013516014A JP2013516014A JP2013530984A JP 2013530984 A JP2013530984 A JP 2013530984A JP 2013516014 A JP2013516014 A JP 2013516014A JP 2013516014 A JP2013516014 A JP 2013516014A JP 2013530984 A JP2013530984 A JP 2013530984A
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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
- C07D213/60—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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- 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
- C07D213/60—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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
R1は、水素、C1-C4-アルキル、C1-C4-ハロアルキル、アリール、またはヘタリールであり、ここで、最後に述べた2つのラジカルは、非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される置換基により置換されており、
R2、R3およびR4は、独立して、水素、C1-C4-アルキル、C1-C4-ハロアルキル、NR5R6またはアリールであり、ここでアリール基は非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される1、2、3もしくは4つの置換基により置換されており、
または、ラジカルR3およびR4は、それらが結合している炭素原子と一緒に飽和、部分的不飽和もしくは最大不飽和である3-、4-、5-、6-もしくは7-員炭素環または環員としてO、SおよびNから選択される1、2もしくは3のヘテロ原子を含む飽和、部分的不飽和もしくは最大不飽和である3-、4-、5-、6-もしくは7-員複素環を形成し、ここで炭素環または複素環は非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される1、2、3もしくは4つの置換基により置換されており、
R5は、水素、C1-C4-アルキルまたはC1-C4-ハロアルキルであり、
R6は、水素、C1-C4-アルキル、C1-C4-ハロアルキル、フェニルおよびフェニル-C1-C4-アルキルであり、
または、R5およびR6は一緒に直鎖C4-もしくはC5-アルキレンブリッジまたは-CH2CH2OCH2CH2-基もしくは-CH2CH2NR7CH2CH2-基を形成し、
R7は水素またはC1-C4-アルキルである。
Yは独立してハロゲンまたはC1-C4-アルコキシであり、
または式IIIaの化合物中の2つのラジカルYは一緒に-O-(CH2)n-O-基を形成し、ここでアルカンジイル部分-(CH2)n-は非置換またはハロゲンおよびC1-C4-アルキルから選択される1、2もしくは3つの置換基で置換されており、
nは2、3または4である。
c)第2の反応時間経過後、反応混合物を少なくとも1つのアンモニア源で処理する。
Claims (15)
- 式Iの4-ヒドロキシピリジン類の製造方法であり、
R1は、水素、C1-C4-アルキル、C1-C4-ハロアルキル、アリールまたはヘタリールであり、ここで、最後に述べた2つのラジカルは、非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される1、2、3もしくは4つの置換基により置換されており、
R2、R3およびR4は、独立して、水素、C1-C4-アルキル、C1-C4-ハロアルキル、NR5R6またはアリールであり、ここでアリールは非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される1、2、3もしくは4つの置換基により置換されており、
または、ラジカルR3およびR4は、それらが結合している炭素原子と一緒に飽和、部分的不飽和もしくは最大不飽和である3-、4-、5-、6-もしくは7-員炭素環または環の一部分としてO、SおよびNから選択される1、2もしくは3のヘテロ原子を含む飽和、部分的不飽和もしくは最大不飽和である3-、4-、5-、6-もしくは7-員複素環を形成し、ここで炭素環または複素環は非置換またはハロゲン、C1-C4-アルキル、C1-C4-ハロアルキル、C1-C4-アルコキシおよびC1-C4-ハロアルコキシから選択される1、2、3もしくは4つの置換基により置換されており、
R5は、水素、C1-C4-アルキルまたはC1-C4-ハロアルキルであり、
R6は、水素、C1-C4-アルキル、C1-C4-ハロアルキル、フェニルおよびフェニル-C1-C4-アルキルであり、
またはR5およびR6は一緒に直鎖C4-もしくはC5-アルキレンブリッジまたは-CH2CH2OCH2CH2-基もしくは-CH2CH2NR7CH2CH2-基を形成し、
R7は水素またはC1-C4-アルキルである。
上記方法は、
a)式IIの化合物を、式IIIaまたはIIIbの化合物およびアルカリ金属メチラートおよびアルカリ金属エチラートから選択される少なくとも1つの塩基と混合して、反応混合物を形成し、
XはハロゲンまたはC1-C4-アルコキシであり、
Yは独立してハロゲンまたはC1-C4-アルコキシであり、
または式IIIaの化合物中の2つのラジカルYは一緒に-O-(CH2)n-O-基を形成し、ここでアルカンジイル部分-(CH2)n-は非置換またはハロゲンおよびC1-C4-アルキルから選択される1、2もしくは3つの置換基で置換されており、
nは2、3または4である。
b)第1の反応時間経過後、反応混合物を少なくとも1つの酸で処理し、
c)第2の反応時間経過後、反応混合物を少なくとも1つのアンモニア源で処理する、
上記工程を含む、前記製造方法。 - 塩基をアルカリ金属メチラートから選択する、請求項1に記載の方法。
- 塩基がナトリウムメチラートである、請求項2に記載の方法。
- 塩基を一価のC1-C4-アルコールに溶解する、請求項1から3のいずれか1項に記載の方法。
- 一価のC1-C4-アルコールがメタノールである、請求項4に記載の方法。
- 式IIIaの化合物を使用する、請求項1から5のいずれか1項に記載の方法。
- 工程a)、b)およびc)において、いずれの中間化合物も単離することなく実施する、請求項1から6のいずれか1項に記載の方法。
- 酸を鉱酸から選択する、請求項1から7のいずれか1項に記載の方法。
- アンモニア源をアンモニア水溶液、ハロゲン化アンモニウム、カルボン酸アンモニウムおよび硫酸アンモニウムから選択する、請求項1から8のいずれか1項に記載の方法。
- R1が水素、C1-C4-アルキルまたはC1-C4-ハロアルキルである、請求項1から9のいずれか1項に記載の方法。
- R1がC1-C4-パーハロアルキルである、請求項10に記載の方法。
- R2、R3、R4が水素、C1-C4-アルキルまたはC1-C4-ハロアルキルである、請求項1から11のいずれか1項に記載の方法。
- R2、R3、R4が水素である、請求項12に記載の方法。
- 塩素化剤が塩化チオニルまたは塩化ホスホリルである、請求項14に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35712810P | 2010-06-22 | 2010-06-22 | |
US61/357,128 | 2010-06-22 | ||
EP10166877 | 2010-06-22 | ||
EP10166877.0 | 2010-06-22 | ||
PCT/IB2011/052681 WO2011161612A1 (en) | 2010-06-22 | 2011-06-20 | Process for preparing 4-hydroxypyridines |
Publications (2)
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JP2013530984A true JP2013530984A (ja) | 2013-08-01 |
JP5984801B2 JP5984801B2 (ja) | 2016-09-06 |
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JP2013516014A Expired - Fee Related JP5984801B2 (ja) | 2010-06-22 | 2011-06-20 | 4−ヒドロキシピリジン類の製造方法 |
Country Status (8)
Country | Link |
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US (1) | US8716487B2 (ja) |
EP (1) | EP2585436B1 (ja) |
JP (1) | JP5984801B2 (ja) |
CN (1) | CN102947270B (ja) |
BR (1) | BR112012032671A2 (ja) |
ES (1) | ES2539379T3 (ja) |
MX (1) | MX2012014796A (ja) |
WO (1) | WO2011161612A1 (ja) |
Families Citing this family (5)
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CN103664761A (zh) * | 2013-12-06 | 2014-03-26 | 常熟市联创化学有限公司 | 一种4-吡啶酚的制备方法 |
EP3548466B1 (en) | 2016-12-01 | 2022-01-12 | Syngenta Participations AG | Process for preparation of intermediate of pesticidally active heterocyclic derivatives with sulfur containing substituents |
TWI795381B (zh) | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為malt1抑制劑之吡唑衍生物 |
UA128288C2 (uk) | 2018-03-08 | 2024-05-29 | Інсайт Корпорейшн | СПОЛУКИ АМІНОПІРАЗИНДІОЛУ ЯК ІНГІБІТОРИ PI3K-<font face="Symbol">g</font> |
US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52151175A (en) * | 1977-07-06 | 1977-12-15 | Nisshin Flour Milling Co Ltd | Gamma-pyrone and gamma-pyridone derivatives |
JPS58170758A (ja) * | 1983-03-14 | 1983-10-07 | Nisshin Flour Milling Co Ltd | γ−ピリドン誘導体 |
US5292885A (en) * | 1989-08-11 | 1994-03-08 | Isochem | Pyranone, process for its preparation, its use in the preparation of a new pyridinone and a process for the preparation of same |
US5625069A (en) * | 1996-07-22 | 1997-04-29 | Development Center For Biotechnology | Process for preparing 2-cyano-3,5-dimethyl-4-methoxypyridine |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN100383123C (zh) | 2004-03-12 | 2008-04-23 | 南通市东昌化工有限公司 | 4-羟基吡啶的生产方法 |
DE102006059710A1 (de) * | 2006-12-18 | 2008-06-19 | Freie Universität Berlin | Substituierte 4-Hydroxypyridine |
AU2009264385B2 (en) | 2008-06-25 | 2013-05-23 | Basf Se | Method for producing substituted biphenyls |
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2011
- 2011-06-20 CN CN201180031044.5A patent/CN102947270B/zh not_active Expired - Fee Related
- 2011-06-20 ES ES11797708.2T patent/ES2539379T3/es active Active
- 2011-06-20 EP EP11797708.2A patent/EP2585436B1/en active Active
- 2011-06-20 BR BR112012032671A patent/BR112012032671A2/pt not_active IP Right Cessation
- 2011-06-20 US US13/805,567 patent/US8716487B2/en not_active Expired - Fee Related
- 2011-06-20 MX MX2012014796A patent/MX2012014796A/es active IP Right Grant
- 2011-06-20 WO PCT/IB2011/052681 patent/WO2011161612A1/en active Application Filing
- 2011-06-20 JP JP2013516014A patent/JP5984801B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS52151175A (en) * | 1977-07-06 | 1977-12-15 | Nisshin Flour Milling Co Ltd | Gamma-pyrone and gamma-pyridone derivatives |
JPS58170758A (ja) * | 1983-03-14 | 1983-10-07 | Nisshin Flour Milling Co Ltd | γ−ピリドン誘導体 |
US5292885A (en) * | 1989-08-11 | 1994-03-08 | Isochem | Pyranone, process for its preparation, its use in the preparation of a new pyridinone and a process for the preparation of same |
US5625069A (en) * | 1996-07-22 | 1997-04-29 | Development Center For Biotechnology | Process for preparing 2-cyano-3,5-dimethyl-4-methoxypyridine |
Non-Patent Citations (5)
Title |
---|
JPN6015023069; Organic Process Researh & Development 6, 2002, 242-245 * |
JPN6015023070; 'Facile synthesis of caerulomycin E by the formation of 2,2'-bipyridine' Tetrahedron 66, 2010, 5432-5434 * |
JPN6015023071; 'Synthesis of 2-methyl-4H-pyran-4-one' Journal of Organic Chemistry 32(12), 1967, 4105-7 * |
JPN6015023072; 'New method for the synthesis of 4-hydroxy-2-trifluoromethylpyridine' Chemistry of Heterocyclic Compounds Vol.33, No.8, 1997, 995-996 * |
JPN6015023073; 'Chemistry of Keto Acetals: Part II. beta,beta'-Keto Diacetal and' Russian Journal of Organic Chemistry Vol.41, No.8, 2005, 1113-1115 * |
Also Published As
Publication number | Publication date |
---|---|
US20130096312A1 (en) | 2013-04-18 |
US8716487B2 (en) | 2014-05-06 |
BR112012032671A2 (pt) | 2015-09-15 |
EP2585436A1 (en) | 2013-05-01 |
WO2011161612A1 (en) | 2011-12-29 |
ES2539379T3 (es) | 2015-06-30 |
EP2585436B1 (en) | 2015-03-18 |
JP5984801B2 (ja) | 2016-09-06 |
CN102947270A (zh) | 2013-02-27 |
EP2585436A4 (en) | 2014-04-23 |
CN102947270B (zh) | 2015-04-08 |
MX2012014796A (es) | 2013-04-03 |
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