JP2018537407A - 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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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
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Abstract
【化1】
【選択図】なし
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 (19)
- 一般式(I)のピコリンアミドを、
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(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)、
反応させるステップは、相間移動触媒及び無機ハロゲン化物助触媒の存在下で行われる、方法。 - 前記相間移動触媒はクラウンエーテルである、請求項1記載の方法。
- 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、請求項2記載の方法。
- 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2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5記載の方法。
- 反応は、有機溶媒中で行われる、請求項1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7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8記載の方法。
- 反応は、塩基性環境で行われる、請求項1記載の方法。
- 前記塩基性環境は、金属炭酸塩によりもたらされる、請求項10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11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]((3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate])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(chloromethyl isobutyrate)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]((3S,6S,7R,8R)-8-benzyl-3-{[(4-methoxy-3-{[(2-methylpropanoyl)oxy]methoxy}-pyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate])である、請求項1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]((3S,6S,7R,8R)-8-benzyl-3-{[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate])を、イソ酪酸クロロメチル(chloromethyl isobutyrate)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]((3S,6S,7R,8R)-8-benzyl-3-{[(4-methoxy-3-{[(2-methylpropanoyl)oxy]methoxy}-pyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate])及び1つ又は複数の副生成物を生成させる、方法。
- 前記1つ又は複数の副生成物は、一般式VIIの化合物を含む、請求項14記載の方法。
- (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]((3S,6S,7R,8R)-8-benzyl-3-{[(4-methoxy-3-{[(2-methylpropanoyl)oxy]methoxy}-pyridin-2-yl)carbonyl]amino}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate])の収率が、約80%(±2%)以上である、請求項14記載の方法。
- 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、請求項14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14記載の方法。
- 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14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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US (1) | US10144728B2 (ja) |
EP (1) | EP3359153B1 (ja) |
JP (2) | JP6975142B2 (ja) |
KR (1) | KR20180066101A (ja) |
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CA (1) | CA3000198C (ja) |
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Citations (5)
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WO2003064361A1 (en) * | 2002-01-31 | 2003-08-07 | Bromine Compounds Ltd. | Pentabromobenzyl alkyl ethers and their use as fire retardants |
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WO2013036679A1 (en) * | 2011-09-07 | 2013-03-14 | Satori Pharmaceuticals, Inc. | Compounds useful for treating neurodegenerative disorders |
WO2014014933A1 (en) * | 2012-07-20 | 2014-01-23 | Merck Sharp & Dohme Corp. | Hiv treatment with amido-substituted pyrimidinone derivatives |
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US6861930B2 (en) | 2001-11-15 | 2005-03-01 | Eaton Corporation | Transfer switch including a circuit breaker housing |
CN104703984A (zh) * | 2012-05-07 | 2015-06-10 | 陶氏益农公司 | 作为杀真菌剂的大环吡啶-2-甲酰胺 |
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- 2016-10-04 MX MX2018003875A patent/MX2018003875A/es unknown
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Patent Citations (5)
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JPH052271A (ja) * | 1990-11-28 | 1993-01-08 | Fuji Photo Film Co Ltd | 平版印刷版の製造方法 |
JP2005507921A (ja) * | 2001-10-23 | 2005-03-24 | ダウ アグロサイエンシィズ エルエルシー | Uk−2aの誘導体 |
WO2003064361A1 (en) * | 2002-01-31 | 2003-08-07 | Bromine Compounds Ltd. | Pentabromobenzyl alkyl ethers and their use as fire retardants |
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PL3359153T3 (pl) | 2021-07-05 |
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US10144728B2 (en) | 2018-12-04 |
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CO2018003474A2 (es) | 2018-06-12 |
EP3359153B1 (en) | 2020-12-16 |
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US20170096414A1 (en) | 2017-04-06 |
TW201718560A (zh) | 2017-06-01 |
EP3359153A4 (en) | 2019-05-08 |
BR102016023198B1 (pt) | 2021-06-22 |
BR102016023198A2 (pt) | 2017-04-18 |
KR20180066101A (ko) | 2018-06-18 |
IL258386A (en) | 2018-05-31 |
DK3359153T3 (da) | 2021-03-08 |
ES2858364T3 (es) | 2021-09-30 |
JP6975142B2 (ja) | 2021-12-01 |
WO2017062362A9 (en) | 2017-12-28 |
BR102016023198B8 (pt) | 2022-09-06 |
CA3000198A1 (en) | 2017-04-13 |
MX2018003875A (es) | 2018-08-16 |
CN108135890A (zh) | 2018-06-08 |
TWI718187B (zh) | 2021-02-11 |
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