JP6975142B2 - クラウンエーテル触媒を利用した、置換クロロアシラールを用いたピコリンアミドのアルキル化 - Google Patents
クラウンエーテル触媒を利用した、置換クロロアシラールを用いたピコリンアミドのアルキル化 Download PDFInfo
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- JP6975142B2 JP6975142B2 JP2018516450A JP2018516450A JP6975142B2 JP 6975142 B2 JP6975142 B2 JP 6975142B2 JP 2018516450 A JP2018516450 A JP 2018516450A JP 2018516450 A JP2018516450 A JP 2018516450A JP 6975142 B2 JP6975142 B2 JP 6975142B2
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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
- C07D213/06—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
- C07D213/16—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 containing only one pyridine ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
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- 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
- B01J31/0201—Oxygen-containing compounds
- B01J31/0204—Ethers
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- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/44—Allylic alkylation, amination, alkoxylation or analogues
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- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
- B01J2531/002—Materials
- B01J2531/007—Promoter-type Additives
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- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/98—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases
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- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Communicable Diseases (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本出願は、その開示内容がその全体で参照により本明細書に援用される、2015年10月6日に出願された米国仮特許出願第62/237,844号の利益を主張するものである。
R2は、N、O、P及びSからなる群から選択される1〜3のヘテロ原子を含む5から12の原子を含有する複素環であって、炭素数1から6のアルキル基、炭素数1から6のアシル基、=O基、ベンジル基、炭素数1から6のアルキルエーテル又はアリールエーテル(aryl ether)からなる群から選択される1つ又は複数の置換基をもつ複素環であり、
R3は、第1級アルキル基、第2級アルキル基又は第3級アルキル基である。)
Claims (16)
- 一般式(I)のピコリンアミドを、
一般式(II)の置換クロロアシラールと反応させて、
一般式(III)の化合物を生成させるステップを含む方法であって
(式中、
R1は、第1級アルキル基又は第2級アルキル基であり、
R2は、N、O、P及びSからなる群から選択される1〜3のヘテロ原子を含む5から12の原子の複素環であって、炭素数1から6のアルキル基、炭素数1から6のアシル基、=O基、ベンジル基、炭素数1から6のアルキルエーテル又はアリールエーテルからなる群から選択される1つ又は複数の置換基をもつ複素環であり、
R3は、第1級アルキル基、第2級アルキル基又は第3級アルキル基である)、
前記反応させるステップは、クラウンエーテル及び無機ハロゲン化物助触媒の存在下で行われ、前記クラウンエーテルは、12−クラウン−4、15−クラウン−5、18−クラウン−6ならびにそれらのベンゾ−クラウンエーテル及びジベンゾ−クラウンエーテルからなる群から選択される、少なくとも1つのエーテルであり、
前記反応は、金属炭酸塩によりもたらされる塩基性環境で行われる、
方法。 - 前記クラウンエーテルは、12−クラウン−4、15−クラウン−5、18−クラウン−6、ベンゾ−12−クラウン−4、ベンゾ−15−クラウン−5及びジベンゾ−18−クラウン−6からなる群から選択される、少なくとも1つのエーテルである、請求項1に記載の方法。
- 前記クラウンエーテルは、15−クラウン−5、18−クラウン−6及びベンゾ−15−クラウン−5からなる群から選択される、少なくとも1つのエーテルである、請求項1に記載の方法。
- 前記無機ハロゲン化物助触媒は、無機ヨウ化物である、請求項1に記載の方法。
- 前記無機ヨウ化物は、ヨウ化ナトリウム及びヨウ化カリウムからなる群から選択される、少なくとも1つのヨウ化物塩である、請求項4に記載の方法。
- 前記反応は、有機溶媒中で行われる、請求項1に記載の方法。
- 前記有機溶媒は、ケトン化合物系、酢酸エステル、芳香族炭化水素、塩素化有機物及び有機ニトリルからなる群から選択される、少なくとも1つの有機溶媒である、請求項6に記載の方法。
- 前記有機溶媒は、アセトン、酢酸エチル及びトルエンからなる群から選択される、少なくとも1つの溶媒である、請求項6に記載の方法。
- 前記金属炭酸塩は、炭酸ナトリウム及び炭酸カリウムからなる群から選択される、少なくとも1つの炭酸塩である、請求項1に記載の方法。
- 前記一般式(I)のピコリンアミドは、(3S,6S,7R,8R)−8−ベンジル−3−{[(3−ヒドロキシ−4−メトキシピリジン−2−イル)カルボニル]アミノ}−6−メチル−4,9−ジオキソ−1,5−ジオキソナン−7−イル 2−メチルプロパノエート]であり、前記一般式(II)の置換クロロアシラールは、イソ酪酸クロロメチルであり、前記一般式(III)の化合物は、(3S,6S,7R,8R)−8−ベンジル−3−{[(4−メトキシ−3−{[(2−メチルプロパノイル)オキシ]メトキシ}−ピリジン−2−イル)カルボニル]アミノ}−6−メチル−4,9−ジオキソ−1,5−ジオキソナン−7−イル 2−メチルプロパノエート]である、請求項1に記載の方法。
- クラウンエーテル及び無機ヨウ化物の存在下で、(3S,6S,7R,8R)−8−ベンジル−3−{[(3−ヒドロキシ−4−メトキシピリジン−2−イル)カルボニル]アミノ}−6−メチル−4,9−ジオキソ−1,5−ジオキソナン−7−イル 2−メチルプロパノエート]を、イソ酪酸クロロメチルと反応させて、(3S,6S,7R,8R)−8−ベンジル−3−{[(4−メトキシ−3−{[(2−メチルプロパノイル)オキシ]メトキシ}−ピリジン−2−イル)カルボニル]アミノ}−6−メチル−4,9−ジオキソ−1,5−ジオキソナン−7−イル 2−メチルプロパノエート]及び1つ又は複数の副生成物を生成させるステップを含む方法であって、前記クラウンエーテルは、12−クラウン−4、15−クラウン−5、18−クラウン−6ならびにそれらのベンゾ−クラウンエーテル及びジベンゾ−クラウンエーテルからなる群から選択される、少なくとも1つのエーテルである、方法。
- 前記クラウンエーテルは、12−クラウン−4、15−クラウン−5、18−クラウン−6、ベンゾ−12−クラウン−4、ベンゾ−15−クラウン−5及びジベンゾ−18−クラウン−6からなる群から選択される、少なくとも1つのエーテルである、請求項11に記載の方法。
- 前記無機ヨウ化物は、ヨウ化ナトリウム及びヨウ化カリウムからなる群から選択される、少なくとも1つのヨウ化物である、請求項11に記載の方法。
- 前記反応は、アセトン、酢酸エチル及びトルエンからなる群から選択される、少なくとも1つの有機溶媒中で行われる、請求項11に記載の方法。
- 前記クラウンエーテルが、15−クラウン−5、18−クラウン−6及びベンゾ−15−クラウン−5からなる群から選択される、少なくとも1つのエーテルである、請求項11に記載の方法。
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JP2021131000A JP2021185157A (ja) | 2015-10-06 | 2021-08-11 | クラウンエーテル触媒を利用した、置換クロロアシラールを用いたピコリンアミドのアルキル化 |
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US201562237844P | 2015-10-06 | 2015-10-06 | |
US62/237,844 | 2015-10-06 | ||
PCT/US2016/055331 WO2017062362A1 (en) | 2015-10-06 | 2016-10-04 | Alkylation of picolinamides with substituted chloroacylals utilizing a crown ether catalyst |
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JP2018537407A JP2018537407A (ja) | 2018-12-20 |
JP6975142B2 true JP6975142B2 (ja) | 2021-12-01 |
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JP2021131000A Pending JP2021185157A (ja) | 2015-10-06 | 2021-08-11 | クラウンエーテル触媒を利用した、置換クロロアシラールを用いたピコリンアミドのアルキル化 |
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US (1) | US10144728B2 (ja) |
EP (1) | EP3359153B1 (ja) |
JP (2) | JP6975142B2 (ja) |
KR (1) | KR20180066101A (ja) |
CN (1) | CN108135890B (ja) |
AR (1) | AR106262A1 (ja) |
BR (1) | BR102016023198B8 (ja) |
CA (1) | CA3000198C (ja) |
CO (1) | CO2018003474A2 (ja) |
DK (1) | DK3359153T3 (ja) |
ES (1) | ES2858364T3 (ja) |
HU (1) | HUE052841T2 (ja) |
IL (1) | IL258386B (ja) |
LT (1) | LT3359153T (ja) |
MX (1) | MX2018003875A (ja) |
PL (1) | PL3359153T3 (ja) |
TW (1) | TWI718187B (ja) |
WO (1) | WO2017062362A1 (ja) |
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US5480762A (en) * | 1990-11-28 | 1996-01-02 | Fuji Photo Film Co., Ltd. | Method for preparing lithographic printing plate |
AR037328A1 (es) * | 2001-10-23 | 2004-11-03 | Dow Agrosciences Llc | Compuesto de [7-bencil-2,6-dioxo-1,5-dioxonan-3-il]-4-metoxipiridin-2-carboxamida, composicion que lo comprende y metodo que lo utiliza |
US6861930B2 (en) | 2001-11-15 | 2005-03-01 | Eaton Corporation | Transfer switch including a circuit breaker housing |
US7091270B2 (en) * | 2002-01-31 | 2006-08-15 | Bromine Compounds Ltd. | Pentabromobenzyl alkyl ethers and their use as fire retardants |
WO2013036679A1 (en) * | 2011-09-07 | 2013-03-14 | Satori Pharmaceuticals, Inc. | Compounds useful for treating neurodegenerative disorders |
BR112014027601A2 (pt) * | 2012-05-07 | 2017-06-27 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
WO2014014933A1 (en) * | 2012-07-20 | 2014-01-23 | Merck Sharp & Dohme Corp. | Hiv treatment with amido-substituted pyrimidinone derivatives |
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BR102016023198A2 (pt) | 2017-04-18 |
BR102016023198B1 (pt) | 2021-06-22 |
TWI718187B (zh) | 2021-02-11 |
CA3000198C (en) | 2024-02-27 |
CN108135890A (zh) | 2018-06-08 |
LT3359153T (lt) | 2021-03-25 |
EP3359153A1 (en) | 2018-08-15 |
WO2017062362A9 (en) | 2017-12-28 |
CO2018003474A2 (es) | 2018-06-12 |
MX2018003875A (es) | 2018-08-16 |
US10144728B2 (en) | 2018-12-04 |
EP3359153B1 (en) | 2020-12-16 |
US20170096414A1 (en) | 2017-04-06 |
ES2858364T3 (es) | 2021-09-30 |
WO2017062362A1 (en) | 2017-04-13 |
BR102016023198B8 (pt) | 2022-09-06 |
TW201718560A (zh) | 2017-06-01 |
CA3000198A1 (en) | 2017-04-13 |
DK3359153T3 (da) | 2021-03-08 |
AR106262A1 (es) | 2017-12-27 |
PL3359153T3 (pl) | 2021-07-05 |
JP2018537407A (ja) | 2018-12-20 |
JP2021185157A (ja) | 2021-12-09 |
EP3359153A4 (en) | 2019-05-08 |
KR20180066101A (ko) | 2018-06-18 |
HUE052841T2 (hu) | 2021-05-28 |
CN108135890B (zh) | 2024-07-09 |
IL258386B (en) | 2021-02-28 |
IL258386A (en) | 2018-05-31 |
ZA201802085B (en) | 2019-06-26 |
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