4-(2-氯吡啶-3-基氨基)哌啶-1-甲酸乙酯 | 906371-78-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(2-氯吡啶-3-基氨基)哌啶-1-甲酸乙酯
• 英文名称: 4-(2-chloropyridin-3-ylamino)piperidine-1-carboxylic acid ethyl ester
• 英文别名: 4-(2-chloro-pyridin-3-ylamino)-piperidine-1-ethyl carboxylate；4-(2-chloro-pyridin-3-ylamino)-piperidine-1-carboxylic acid ethyl ester；ethyl 4-[(2-chloropyridin-3-yl)amino]piperidine-1-carboxylate；Ethyl 4-(2-chloropyridin-3-ylamino)piperidine-1-carboxylate
• CAS: 906371-78-6
• 化学式: C₁₃H₁₈ClN₃O₂
• 分子量: 283.758
• InChiKey: UBZFNANLUWYHJX-UHFFFAOYSA-N

物化性质

• 沸点：
  434.0±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4-(2-氯吡啶-3-基氨基)哌啶-1-甲酸乙酯 在 palladium diacetate 、 potassium carbonate 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 异丙醇 为溶剂， 反应 22.0h， 生成 4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  NOVEL HETEROCYCLIC COMPOUNDS AND USE THEREOF IN MEDICINE AND IN COSMETICS

  摘要：

  这项发明涉及一般式(I)的新型杂环化合物，以及它们的药用盐和对映体。该发明还涉及将其用作药物产品，优选用于预防和/或治疗具有神经源性成分的炎症性疾病，或将其用作化妆品。本发明的化合物作为CGRP-R受体的拮抗剂。

  公开号：

  US20180050992A1
• 作为产物：
  描述：

  4-[1-(2-chloro-pyridin-3-yl)ureido]piperidine-1-carboxylic acid ethyl ester 在 lithium hexamethyldisilazane 作用下， 以95%的产率得到4-(2-氯吡啶-3-基氨基)哌啶-1-甲酸乙酯
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j

文献信息

• Process for the preparation of Caprolactam Cgrp Antagonist
  申请人：Palucki Michael

  公开号：US20090124799A1

  公开（公告）日：2009-05-14

  An efficient syntheses for the preparation of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one.

  一种高效合成方法，用于制备(3R,6S)-3-氨基-6-(2,3-二氟苯基)-1-(2,2,2-三氟乙基)氮杂七环-2-酮。
• Process for the Preparation of Cgrp Antagonist
  申请人：Belyk Kevin

  公开号：US20090281306A1

  公开（公告）日：2009-11-12

  An efficient synthesis for the preparation of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide, by coupling (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride with 1,1′-carbonyldiimidazole (“CDI”) as carbonyl source; and an efficient preparation of the potassium salt of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide.

  一种高效的合成方法，用于制备N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂丙酰胺基]-4-(2-氧代-2,3-二氢-1H-咪唑并[4,5-b]吡啶-1-基)哌啶-1-羧酰胺，通过将(3R,6S)-3-氨基-6-(2,3-二氟苯基)-1-(2,2,2-三氟乙基)氮杂丙酮和2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑并[4,5-b]吡啶二盐酸盐与1,1'-羰基二咪唑（“CDI”）作为羰基源进行偶联；以及一种高效的制备钾盐的方法N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂丙酰胺基]-4-(2-氧代-2,3-二氢-1H-咪唑并[4,5-b]吡啶-1-基)哌啶-1-羧酰胺。
• CGRP Antagonist Salt
  申请人：Belyk Kevin

  公开号：US20100286122A1

  公开（公告）日：2010-11-11

  An efficient synthesis for the preparation of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin- 1 -yl)piperidine-1-carboxamide, by coupling (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride with 1,1′-carbonyldiimidazole (“CDI”) as carbonyl source; an efficient preparation of the potassium salt of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin- 1 -yl)piperidine-1-carboxamide; efficient syntheses for the preparation of intermediates (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride, and the potassium salt of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide including the potassium salt ethanolate and potassium salt hydrate.

  一种高效合成方法，用于制备N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂七环-3-基]-4-(2-氧代-2,3-二氢-1H-咪唑[4,5-b]吡啶-1-基)哌啶-1-羧酰胺，通过将(3R,6S)-3-氨基-6-(2,3-二氟苯基)-1-(2,2,2-三氟乙基)氮杂七环-2-酮和2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑[4,5-b]吡啶二盐酸盐与1,1'-羰基二咪唑（“CDI”）做为羰基源进行偶联；一种高效制备钾盐的方法，用于制备N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂七环-3-基]-4-(2-氧代-2,3-二氢-1H-咪唑[4,5-b]吡啶-1-基)哌啶-1-羧酰胺；高效合成方法，用于制备中间体(3R,6S)-3-氨基-6-(2,3-二氟苯基)-1-(2,2,2-三氟乙基)氮杂七环-2-酮和2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑[4,5-b]吡啶二盐酸盐，以及N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂七环-3-基]-4-(2-氧代-2,3-二氢-1H-咪唑[4,5-b]吡啶-1-基)哌啶-1-羧酰胺的钾盐乙醇酸盐和钾盐水合物的高效制备方法。
• Process for the preparation of CGRP antagonist
  申请人：Merck Sharp & Dohme Corp.

  公开号：US07829699B2

  公开（公告）日：2010-11-09

  An efficient synthesis for the preparation of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1 -carboxamide, by coupling (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride with 1,1′-carbonyldiimidazole (“CDI”) as carbonyl source; and an efficient preparation of the potassium salt of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide.

  一种高效的合成方法，用于制备N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂七环-3-基]-4-(2-氧代-2,3-二氢-1H-咪唑[4,5-b]吡啶-1-基)哌啶-1-羧酰胺，通过将(3R,6S)-3-氨基-6-(2,3-二氟苯基)-1-(2,2,2-三氟乙基)氮杂七环-2-酮和2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑[4,5-b]吡啶二盐酸盐与1,1'-碳酰二咪唑（“CDI”）作为羰基源进行偶联；以及N-[(3R,6S)-6-(2,3-二氟苯基)-2-氧代-1-(2,2,2-三氟乙基)氮杂七环-3-基]-4-(2-氧代-2,3-二氢-1H-咪唑[4,5-b]吡啶-1-基)哌啶-1-羧酰胺的钾盐的高效制备。
• Process for the Preparation of Pyridine Heterocycle Cgrp Antagonist Intermediate
  申请人：McLaughlin Mark

  公开号：US20090176986A1

  公开（公告）日：2009-07-09

  An efficient syntheses for the preparation of the intermediate 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride, and other salt forms of 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine.

  一种高效的合成方法，用于制备中间体2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑[4,5-b]吡啶二盐酸盐，以及其他盐酸盐形式的2-氧代-1-(4-哌啶基)-2,3-二氢-1H-咪唑[4,5-b]吡啶。