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TW201609694A - 用於製備３－（３－氯－１ｈ－吡唑－１－基）吡啶的方法（一） - Google Patents

用於製備３－（３－氯－１ｈ－吡唑－１－基）吡啶的方法（一） Download PDF

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TW201609694A
TW201609694A TW104124373A TW104124373A TW201609694A TW 201609694 A TW201609694 A TW 201609694A TW 104124373 A TW104124373 A TW 104124373A TW 104124373 A TW104124373 A TW 104124373A TW 201609694 A TW201609694 A TW 201609694A
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pyrazol
pyridine
chloro
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小永 李
強 楊
葛雷 羅斯
貝絲 羅斯貝奇
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陶氏農業科學公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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

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Abstract

3-(3-氯-1H-吡唑-1-基)吡啶之製備係藉由使用商業上可得的3-乙氧基丙烯腈來環化3-肼基吡啶-·二鹽酸鹽來提供3-(3-胺基-1H-吡唑-1-基)吡啶，以及藉由透過山德邁耳反應(Sandmeyer reaction)而將胺基轉化成氯基。

Description

用於製備3-(3-氯-1H-吡唑-1-基)吡啶的方法(一) 相關申請案之交叉引述
此申請案主張2014年7月31日提申之美國專利臨時申請案第62/031,533號之利益，其之整體揭示在此明確地併入此申請案以作為參考資料。
本發明係有關於用於製備3-(3-氯-1H-吡唑-1-基)吡啶的改良方法。
發明背景
US 20130288893(A1)描述尤其是某些(3-鹵(halo)-1-(吡啶-3-基)-1H-吡唑-4-基)醯胺及胺甲酸酯類以及其等作為殺蟲劑之用途。製備此等化合物之路徑涉及製備3-(3-氯-1H-吡唑-1-基)吡啶(5b)，其係藉由直接偶合3-溴吡啶及3-氯吡唑來進行。3-氯吡唑之製備係藉由a)用2-二甲基胺磺醯氯及氫化鈉來處理1H-吡唑，以提供N,N-二甲基-1H-吡唑-1-磺醯胺，b)用六氯乙烷及正丁基鋰來處理N,N-二甲基-1H-吡唑-1-磺醯胺，以提供3-氯-N,N-二甲基-1H-吡唑-1-磺醯胺，以及c)用三氟乙酸從3-氯-N,N-二甲基-1H-吡唑-1-磺醯胺移除N,N-二甲基磺醯胺，以提供3-氯吡唑。
該揭示的方法生產的產量低，依賴的起始材料不易製備(3-氯吡唑)，以及提供的產物不易單離成純的形式。會希望有一種用於製備3-(3-氯-1H-吡唑-1-基)吡啶的方法，其能避開此等問題。
發明概要
本發明提供此一種替代方案，其係藉由使用商業上可得的3-乙氧基丙烯腈來環化3-肼基吡啶-·二鹽酸鹽來提供3-(3-胺基-1H-吡唑-1-基)吡啶(8a)，以及藉由透過山德邁耳反應(Sandmeyer reaction)而將胺基轉化成氯基。因而，本發明係關於用於製備3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法，
該方法包含a)於一種鹼金屬(C1-C4)烷氧化物存在下，在大約25℃至大約100℃的溫度下，於一種(C1-C4)脂族醇中用3-乙氧基丙烯腈
來處理3-肼基吡啶·二鹽酸鹽 ，以提供3-(3-胺基-1H-吡唑-1-基)吡啶(8a) b)在大約0℃至大約25℃的溫度下，於含水鹽酸中用亞硝酸鈉來處理3-(3-胺基-1H-吡唑-1-基)吡啶(8a)，以提供重氮鹽(8b)；以及c)在大約0℃至大約25℃的溫度下，用氯化銅來處理重氮鹽(8b)。
較佳實施例之詳細說明
本發明提供用於製備3-(3-氯-1H-吡唑-1-基)吡啶(5b)的改良方法，其係藉由使用商業上可得的3-乙氧基丙烯腈來環化3-肼基吡啶·二鹽酸鹽來提供3-(3-胺基-1H-吡唑 -1-基)吡啶(8a)，以及藉由透過山德邁耳反應(Sandmeyer reaction)而將胺基轉化成氯基。
於第一個步驟中，於一種鹼金屬(C1-C4)烷氧化物存在下，在大約25℃至大約100℃的溫度下，於一種(C1-C4)脂族醇中用3-乙氧基丙烯腈來處理3-肼基吡啶·二鹽酸鹽，以提供3-(3-胺基-1H-吡唑-1-基)吡啶(8a)。雖然要求化學計量的3-肼基吡啶·二鹽酸鹽及3-乙氧基丙烯腈，但是通常使用大約1.5倍至大約2倍過量的3-乙氧基-丙烯腈是合宜的。環化作用是在一種鹼金屬(C1-C4)烷氧化物鹼存在下進行。通常使用大約2倍至大約5倍過量的鹼是合宜的。環化作用是在一種(C1-C4)脂族醇類中進行。相同的烷氧化物鹼和醇溶劑是最合宜的，舉例而言，配於乙醇中的乙氧化鈉。瞭解到甲氧基丙烯腈和丙氧基丙烯腈會適合達成環化作用。
於典型的反應中，將3-肼基吡啶·二鹽酸鹽及無水酒精引進一反應器皿中，以及逐步添加烷氧化物鹼。攪拌混合物且添加3-乙氧基丙烯腈。混合物係於80℃下攪拌直到大部分的3-肼基吡啶反應。讓混合物冷卻，以及用酸來中和過量的鹼。用標準技術合宜地單離及純化粗製3-(3-胺基-1H-吡唑-1-基)吡啶(8a)。
3-(3-胺基-1H-吡唑-1-基)吡啶(8a)繼而轉化成所欲的3-(3-氯-1H-吡唑-1-基)吡啶(5b)，其係藉由在大約0℃至大約25℃的溫度下，於含水鹽酸中用亞硝酸鈉來處理，以提供重氮鹽，然後在大約0℃至大約25℃的溫度 下，用氯化銅來處理重氮鹽。雖然要求化學計量的試劑，但是通常使用對於3-(3-胺基-1H-吡唑-1-基)吡啶(8a)為過量的試劑是合宜的。因而，使用大量過量的含水鹽酸作為反應基質。使用大約1.3倍至大約2倍過量的亞硝酸鈉。使用大約5莫耳百分比至大約60莫耳百分比過量的氯化銅，較佳為大約15莫耳百分比至大約30莫耳百分比過量的氯化銅。氯化銅可以為氯化銅(I)或氯化銅(II)。為了抑制反應期間的發泡，在用氯化銅來處理重氮鹽的期間，可以添加與水不混溶的有機溶劑，例如甲苯或氯仿。
於典型的反應中，將3-(3-胺基-1H-吡唑-1-基)吡啶(8a)及含水鹽酸的混合物混合，以及冷卻至大約0℃。緩慢地添加亞硝酸鈉水溶液，溫度維持在大約5℃以下。在大約0℃下攪拌懸浮液歷時大約2小時。於單獨的器皿中，將氯化銅(I)及甲苯的混合物冷卻至大約0℃，以及以溫度維持在大約5℃以下的速率來添加冷卻的重氮鹽懸浮液。讓混合物加溫至大概周圍溫度。反應完成之後，用含水氫氧化鈉來處理混合物以調整冷卻pH至大約8到大約10。用與水不混溶的有機溶劑來萃取生成的溶液。移除溶劑之後，3-(3-氯-1H-吡唑-1-基)吡啶(5b)可以直接使用於下一個步驟，或是用例如急速管柱層析法或結晶之標準技術來進一步純化。
提出下列實施例來闡釋本發明。
實施例 1. 3-(3-胺基-1H-吡唑-1-基)吡啶(8a)之製備
將3-肼基吡啶·二鹽酸鹽(1.82g，10.0mmol)及無水酒精(10.0mL)引進至裝備有回流冷凝器之三頸的圓底燒瓶(50mL)內。於5分鐘期間添加乙氧化鈉(21wt%配於EtOH，11.8mL，31.5mmol)，以及內溫由23℃增加至30℃。在攪拌10分鐘之後，生成的淺棕色漿體轉變成淺粉紅色。於5分鐘期間添加3-乙氧基丙烯腈(2.06mL，20.0mmol)，以及內溫保持在30℃。黃色混合物係於氮氣下在78℃下攪拌歷時5小時，然後冷卻至15℃。緩慢地添加鹽酸(4M配於1,4-二噁烷(dioxane)，2.90mL)來驟冷任何過量的鹼，形成淺棕色懸浮液。混合物係於減壓下濃縮，以提供棕色固體。將固體分配於水(30mL)及乙酸乙酯(50mL)。經由過濾來收集不溶的淺棕色固體，以提供第一部分的產物(0.340g，依據1H NMR為>95%純的)。用乙酸乙酯(3×50mL)萃取水層。組合的有機萃取物係予以濃縮，以提供深棕色潮濕的固體。將混合物懸浮於乙酸乙酯(10mL)、過濾，以及用庚烷(20mL)來清洗，以提供如棕色固體之第二部分的產物(1.00g，依據1H NMR為>95%純的)。獲得如棕色固體之標題化合物(1.34g，84%)：1H NMR(400MHz,DMSO-d 6 )δ 8.93(d,J=2.4Hz,1H),8.33(dd,J=4.8,1.2Hz,1H),8.23(d,J=2.4Hz,1H),8.01(ddd,J=8.4, 2.8,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),5.80(d,J=2.4Hz,1H),5.19(bs,2H,-NH2)；13C NMR(100MHz,DMSO-d 6 )δ 157.7,144.7,138.0,136.2,128.3,123.9,123.2,97.1；EIMS m/z 160([M]+)；HPLC(Zorbax SB-C8管柱，P/N：863954-306；移動相：A=水(0.1%蟻酸)，B=乙腈(0.01%蟻酸)；梯度由5至100%乙腈於15分鐘期間，流量：1.0mL/分鐘)：tR=1.95分鐘。
2. 3-(3-氯-1H-吡唑-1-基)吡啶(5b)之製備
將3-(3-胺基-1H-吡啶基)-吡唑(0.480g，3.00mmol)及濃鹽酸(4.6mL)裝至三頸的圓底燒瓶(25mL)內。使用氯化鈉冰浴讓劇烈攪拌的混合物冷卻至-5℃。於40分鐘期間逐滴地添加配於水(1.3mL)之亞硝酸鈉(0.269g，3.90mmol)，同時溫度維持在-5℃。生成的深橘色混合物在-5℃和0℃之間攪拌歷時1小時，然後在25℃下，於15分鐘期間逐滴地添加至配於氯仿(4.8mL)之氯化銅(I)(0.475g，4.80mmol)懸浮液。深綠色漿體於室溫下攪拌歷時1小時。混合物添加水(10mL)和氯仿(10mL)，產生深綠色溶液。用氫氧化鈉(50%配於水)來中和酸性水溶液成pH 8，以及用氯仿(2×10mL)和乙酸乙酯(3×20mL)來萃取。組合的有機萃取物係於無水硫酸鈉上乾燥、於減壓下濃縮， 以提供如黃色固體之粗產物(0.476g)。LC分析使用鄰苯二甲酸二正丙酯作為內標準，指示73.7%純度(0.351g，65%)：1H NMR(400MHz,CDCl3)δ 8.94(d,J=2.8Hz,1H),8.57(dd,J=4.8,1.2Hz,1H),8.03(ddd,J=8.4,2.8,1.6Hz,1H),7.90(d,J=2.4Hz,1H),7.41(ddd,J=8.4,4.8,0.8Hz,1H),6.45(d,J=2.4Hz,1H)；EIMS m/z 179([M]+)；HPLC(Zorbax SB-C8管柱，P/N：863954-306；移動相：A=水(0.1%蟻酸)，B=乙腈(0.01%蟻酸)；梯度由5至100%乙腈於15分鐘期間，流量：1.0mL/分鐘)：tR=6.28分鐘。

Claims (2)

  1. 一種用於製備3-(3-氯-1H-吡唑-1-基)吡啶(5b)的方法， 該方法包含a)於一鹼金屬(C1-C4)烷氧化物存在下，在大約25℃至大約100℃的溫度下，於(C1-C4)脂族醇中用3-乙氧基丙烯腈 來處理3-肼基吡啶·二鹽酸鹽 ，以提供3-(3-胺基-1H-吡唑-1-基)吡啶(8a) b)在大約0℃至大約25℃的溫度下，於含水鹽酸 中用亞硝酸鈉來處理該3-(3-胺基-1H-吡唑-1-基)吡啶(8a)，以提供重氮鹽(8b)；以及c)在大約0℃至大約25℃的溫度下，用氯化銅來處理該重氮鹽(8b)。
  2. 如請求項1之方法，其中於步驟c)中添加與水不混溶的有機溶劑來抑制發泡。
TW104124373A 2014-07-31 2015-07-28 用於製備３－（３－氯－１ｈ－吡唑－１－基）吡啶的方法（一） TW201609694A (zh)

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US20180030029A1 (en) 2018-02-01
BR112017000293A2 (pt) 2017-10-31
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