tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate | 335255-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate
• 英文别名: 3-(2-Cyano-pyridin-4-yl)-3-oxo-propionic acid tert.-but yl ester；3-(2-Cyano-pyridin-4-yl)-3-oxo-propionic acid tert-butyl ester
• CAS: 335255-95-3
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: QQJNABOVYNTCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 4-(8-fluoro-2-oxo-2,3-dihydro-1H-benzo[b][1,4]diazepin-4-yl)picolinonitrile
  参考文献：
  名称：

  A combination of flow and batch mode processes for the efficient preparation of mGlu2/3 receptor negative allosteric modulators (NAMs)

  摘要：

  Benzodiazepinones are privileged scaffolds with activity against multiple therapeutically relevant biological targets. In support of our ongoing studies around allosteric modulators of metabotropic glutamate receptors (mGlus) we required the multigram synthesis of a beta-ketoester key intermediate. We report the continuous flow synthesis of tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate and its transformation to potent mGlu(2/3) negative allosteric modulators (NAMs) in batch mode. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.03.068
• 作为产物：
  描述：

  甲基异烟酸-N-氧化物 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， -30.0~150.0 ℃ 、800.01 kPa 条件下， 生成 tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate 、
  参考文献：
  名称：

  A combination of flow and batch mode processes for the efficient preparation of mGlu2/3 receptor negative allosteric modulators (NAMs)

  摘要：

  Benzodiazepinones are privileged scaffolds with activity against multiple therapeutically relevant biological targets. In support of our ongoing studies around allosteric modulators of metabotropic glutamate receptors (mGlus) we required the multigram synthesis of a beta-ketoester key intermediate. We report the continuous flow synthesis of tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate and its transformation to potent mGlu(2/3) negative allosteric modulators (NAMs) in batch mode. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.03.068

文献信息

• Glutamate receptor antagonists
  申请人：Hoffmann-la Roche Inc.

  公开号：US06407094B1

  公开（公告）日：2002-06-18

  The present invention relates to compounds of with a base structure of formula 1 The compounds of formula I are shown to have activity as metabotropic glutamate receptor antagonists.

  这项发明涉及具有公式1的基本结构的化合物。 公式I的化合物被证明具有作为代谢型谷氨酸受体拮抗剂的活性。
• Dihydro-benzo [b][1,4]diazepin-2-one derivatives
  申请人：Hoffman-La Roche Inc.

  公开号：US06544985B2

  公开（公告）日：2003-04-08

  This invention is a dihydro-benzo[b][1,4]diazepin-2-one derivative of the formula wherein R1, R2, R3, X and Y are as defined in the specification. The invention includes pharmaceutical compositions containing these compounds, a process for their preparation, their use in preparation of pharmaceutical compositions and administration of an effective amount of the compounds for the treatment or prevention of acute and/or chronic neurological disorders to a patient in need of such treatment.

  这项发明是一种具有以下结构的二氢苯并[b][1,4]二氮杂环己酮衍生物的公式 其中R1、R2、R3、X和Y如规范中定义。该发明包括含有这些化合物的药物组合物，其制备方法，它们在制备药物组合物和向需要此类治疗的患者施用有效量的化合物以治疗或预防急性和/或慢性神经系统疾病的用途。
• Dihydro-benzo [b] [1,4] diazepin-2-one derivatives
  申请人：——

  公开号：US20020198197A1

  公开（公告）日：2002-12-26

  This invention is a dihydro-benzo [b] [1,4] diazepin-2-one derivative of the formula 1 wherein R 1 , R 2 , R 3 and Y are as defined in the specification. The invention includes pharmaceutical compositions containing these compounds, a process for their preparation and a method of treatment or prevention of acute and/or chronic neurological disorders by administering an effective amount of the compound of formula I or a pharmaceuticall acceptable salt thereof.

  这项发明是一种二氢苯并[1,4]二氮杂环己-2-酮衍生物，其化学式如下所示：其中R1、R2、R3和Y的定义如规范中所述。该发明包括含有这些化合物的药物组合物，其制备方法以及通过给予化合物I或其药用可接受盐的有效剂量来治疗或预防急性和/或慢性神经系统疾病的方法。
• Dihydro-benzo [B] [1,4] diazepin-2-one derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06548495B2

  公开（公告）日：2003-04-15

  This invention is a dihydro-benzo[b][1,4]diazepin-2-one derivative of the formula wherein R1, R2, R3 and Y are as defined in the specification. The invention includes pharmaceutical compositions containing these compounds, a process for their preparation and a method of treatment or prevention of acute and/or chronic neurological disorders by administering an effective amount of the compound of formula I or a pharmaceuticall acceptable salt thereof.

  这项发明涉及一种二氢苯并[b][1,4]二氮杂烷-2-酮衍生物，其化学式中的R1、R2、R3和Y如规范中所定义。该发明包括含有这些化合物的药物组合物、其制备方法以及通过给予公式I化合物或其药学上可接受的盐的有效量来治疗或预防急性和/或慢性神经系统疾病的方法。
• BENZODIAZEPINE DERIVATIVES AS METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1224175B1

  公开（公告）日：2004-03-17