CN112724132B - 一种3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶的合成方法 - Google Patents
一种3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶的合成方法 Download PDFInfo
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- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims abstract description 4
- JQUBKTQDNVZHIY-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonohydrazide Chemical compound CC1=CC(C)=C(S(=O)(=O)NN)C(C)=C1 JQUBKTQDNVZHIY-UHFFFAOYSA-N 0.000 claims abstract description 3
- IIYVNMXPYWIJBL-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1 IIYVNMXPYWIJBL-UHFFFAOYSA-N 0.000 claims abstract description 3
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- 238000006243 chemical reaction Methods 0.000 abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 229940079593 drug Drugs 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
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- 150000005229 pyrazolopyridines Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- KQNACZWCHZBAAZ-UHFFFAOYSA-N (sulfonylamino)amine;toluene Chemical compound NN=S(=O)=O.CC1=CC=CC=C1 KQNACZWCHZBAAZ-UHFFFAOYSA-N 0.000 description 1
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- WQHINJAXBRHIJX-UHFFFAOYSA-N N1=CC=CC=C1.CF Chemical compound N1=CC=CC=C1.CF WQHINJAXBRHIJX-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
本发明提供了一种3‑卤代‑5‑三氟甲基‑吡唑并[1,5‑a]吡啶的合成方法。本发明属于医药化学合成领域。本发明以4‑三氟甲基吡啶为原料与2,4,6‑三甲基苯磺酰肼反应成盐,再与丙炔酸乙酯反应得到中间体3,中间体3在酸作用下水解得到中间体4,中间体4与NXS反应得到3‑卤代‑5‑三氟甲基‑吡唑并[1,5‑a]吡啶5。其中X为:Cl、Br、I中的任意一种。本发明反应步骤少、操作简单,原料便宜易得且目标化合物为新化合物无合成报道,系我们首次发明。
Description
技术领域:
本发明涉及一种医药中间体的合成方法,具体而言,本发明涉及一种3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶的合成方法。
技术背景
吡唑并吡啶衍生物是一类非常重要的含氮杂环化合物,广泛的用于医药和农药领域。药理学研究表明,这类化合物具有杀菌、抗真菌、抗肿瘤、止痛、抗血小板等诸多活性,在防治克氏阴性和阳性细菌、各种恶性肿瘤、神经性疾病、骨质疏松症和老年痴呆症等方面疗效显著。在农药领域,杂环化合物已成为农药发展的新主流,使农药进入超高效、无公害的绿色农药新时代。吡唑并吡啶类衍生物主要有吡唑并[3,4-a]吡啶、吡唑并[1,5-a]吡啶、吡唑并[4,3-a]吡啶等三类,而研究最多的当属吡唑并[1,5-a]吡啶系列化合物。
发明内容
本发明提供了一种3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶的合成方法。本发明属于医药化学合成领域。本发明以4-三氟甲基吡啶为原料与2,4,6-三甲基苯磺酰肼反应成盐,再与丙炔酸乙酯反应得到中间体3,中间体3在酸作用下水解得到中间体4,中间体4与NXS反应得到3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶5。其中X为:Cl、Br、I中的任意一种。其合成路线为:
本发明所用的原料和试剂均市售可得。
1.本发明的要点在于:发明了一种3-卤代-5-三氟甲基-吡唑并[1,5-a]吡啶新化合物。
2.本发明的优势是:(1)本发明反应步骤少、操作简单,原料便宜易得且目标化合物为新化合物无合成报道,系我们首次发明;(2)本发明化合物具有很好的体外抗结核病菌活性,药代动力学实验同样性质良好而且毒副作用很低,具有很好的成药性。
下面通过实例对本发明作进一步的描述,本领域的技术人员应理解,所举实例只用于解释本发明,并非用于限定本发明的保护范围。
具体实施方案
实施例1:3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶的合成
1. 5-三氟甲基-吡唑并[1,5-a]-3-羧酸乙酯(中间体3)的合成
将1.47g 4-三氟甲基吡啶溶于10ml二氯甲烷中,0℃条件下缓慢分批次加入新买的2.14g 2,4,6-三甲基苯磺酰肼,反应2h后,将溶液减压蒸干。将残余物溶于干燥的20mlN,N-二甲基甲酰胺中,再加入2.76g碳酸钾,搅拌溶清,逐滴加入丙炔酸乙酯0.98g,室温下搅拌反应过夜。TLC检测反应完全后,将反应液用水稀释,乙酸乙酯萃取。所得有机相再用水和饱和食盐水洗涤,无水硫酸钠干燥,有机相减压蒸干。残余物通过柱层析纯化,得到中间体3(1.03g,产率40%)为类白色固体。
2. 5-三氟甲基-吡唑并[1,5-a]吡啶(中间体4)的合成
将0.9g中间体3在10ml 40%的硫酸溶液中回流3小时,TLC检测反应完全后,冷却至室温,用2N NaOH溶液调节其PH=8。乙酸乙酯萃取,所得有机相再用饱和食盐水洗涤,无水硫酸钠干燥,有机相减压蒸干。残余物通过柱层析纯化,得到中间体4(0.54g,产率83%)为类白色固体。
3. 3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶(化合物5)的合成
将0.52g中间体4溶于8ml乙腈中,分批次加入0.69g NIS,升温至回流反应1h。TLC检测反应完全后,将反应液倒入水中,甲基叔丁基醚萃取,所得有机相再用2N NaOH溶液,15%硫代硫酸钠和饱和食盐水洗涤,无水硫酸钠干燥,有机相减压蒸干。残余物通过柱层析纯化,得到化合物5(0.75g,产率86%)为淡黄色固体。1H NMR(400MHz,CDCl3)δ8.44(d,J=7.2Hz,1H),7.94(s,1H),7.43(s,1H),6.83(d,J=7.2Hz,1H)。
实施例2:3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶的生物活性
(1)本发明所述的3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶具有很好的体外抗结核病菌活性,化合物最小抑菌浓度仅为0.005μg/mL。对于耐多药结核菌菌株抑制作用非常显著。体内实验结果显示,本发明所述的3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶在5mg/kg/d的剂量下,就可完全清除小鼠体内H37Ra的感染量。
(2)本发明所述的3-碘-5-三氟甲基-吡唑并[1,5-a]吡啶的药代动力学实验同样性质良好而且很低的毒副作用,具有很好的成药性,发展前景显著。
本发明不限于上述实例。以上所述仅为本发明的实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
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CN105524058A (zh) * | 2014-10-21 | 2016-04-27 | 中国科学院广州生物医药与健康研究院 | 吡唑并[1,5-a]吡啶类化合物及其应用 |
CN107163043A (zh) * | 2017-06-16 | 2017-09-15 | 上海毕得医药科技有限公司 | 一种吡唑并[1,5‑a]吡啶‑3‑羧酸酯衍生物的合成方法 |
CN108884091A (zh) * | 2016-03-10 | 2018-11-23 | 日产化学株式会社 | 稠合杂环化合物和有害生物防除剂 |
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CN105524058A (zh) * | 2014-10-21 | 2016-04-27 | 中国科学院广州生物医药与健康研究院 | 吡唑并[1,5-a]吡啶类化合物及其应用 |
CN108884091A (zh) * | 2016-03-10 | 2018-11-23 | 日产化学株式会社 | 稠合杂环化合物和有害生物防除剂 |
CN107163043A (zh) * | 2017-06-16 | 2017-09-15 | 上海毕得医药科技有限公司 | 一种吡唑并[1,5‑a]吡啶‑3‑羧酸酯衍生物的合成方法 |
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