3,5-dibromo-N,N-dimethylpyridin-2-amine | 84539-28-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,5-dibromo-N,N-dimethylpyridin-2-amine
• 英文别名: (3,5-dibromo-pyridin-2-yl)-dimethyl-amine；(3,5-dibromo-[2]pyridyl)-dimethyl-amine；(3,5-Dibrom-[2]pyridyl)-dimethyl-amin
• CAS: 84539-28-6
• 化学式: C₇H₈Br₂N₂
• 分子量: 279.962
• InChiKey: YJTQLFURLIUILE-UHFFFAOYSA-N

物化性质

• 熔点：
  41-43 °C
• 沸点：
  285.9±40.0 °C(Predicted)
• 密度：
  1.829±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-dibromo-N,N-dimethylpyridin-2-amine 、 4-氨基甲酰苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 4-(5-bromo-2-(dimethylamino)pyridin-3-yl)benzamide
  参考文献：
  名称：

  Identification and characterisation of 2-aminopyridine inhibitors of checkpoint kinase 2

  摘要：

  5-(Hetero)aryl-3-(4-carboxamidophenyl)-2-aminopyridine inhibitors of CHK2 were identified from high throughput screening of a kinase-focussed compound library. Rapid exploration of the hits through straightforward chemistry established structure-activity relationships and a proposed ATP-competitive binding mode which was verified by X-ray crystallography of several analogues bound to CHK2. Variation of the 5-(hetero)aryl substituent identified bicyclic dioxolane and dioxane groups which improved the affinity and the selectivity of the compounds for CHK2 versus CHK1. The 3-(4-carboxamidophenyl) substituent could be successfully replaced by acyclic omega-aminoalkylamides, which made additional polar interactions within the binding site and led to more potent inhibitors of CHK2. Compounds from this series showed activity in cell-based mechanistic assays for inhibition of CHK2.

  DOI：

  10.1016/j.bmc.2009.11.058
• 作为产物：
  描述：

  2-二甲氨基吡啶 在 1,3-二溴-5,5-二甲基海因 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以54%的产率得到3,5-dibromo-N,N-dimethylpyridin-2-amine
  参考文献：
  名称：

  Identification and characterisation of 2-aminopyridine inhibitors of checkpoint kinase 2

  摘要：

  5-(Hetero)aryl-3-(4-carboxamidophenyl)-2-aminopyridine inhibitors of CHK2 were identified from high throughput screening of a kinase-focussed compound library. Rapid exploration of the hits through straightforward chemistry established structure-activity relationships and a proposed ATP-competitive binding mode which was verified by X-ray crystallography of several analogues bound to CHK2. Variation of the 5-(hetero)aryl substituent identified bicyclic dioxolane and dioxane groups which improved the affinity and the selectivity of the compounds for CHK2 versus CHK1. The 3-(4-carboxamidophenyl) substituent could be successfully replaced by acyclic omega-aminoalkylamides, which made additional polar interactions within the binding site and led to more potent inhibitors of CHK2. Compounds from this series showed activity in cell-based mechanistic assays for inhibition of CHK2.

  DOI：

  10.1016/j.bmc.2009.11.058

文献信息

• A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid
  作者：A. N. Sanzhiev、M. I. Potapova、E. A. Krasnokutskaya、V. D. Filimonov

  DOI：10.1134/s1070428020060093

  日期：2020.6

  reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic

  摘要在三氟甲磺酸的存在下氨基吡啶的重氮化可得到相应的吡啶基三氟甲磺酸盐，而不是预期的重氮盐。在二甲基甲酰胺中加热时，通过取代三氟甲磺酰氧基，可以将吡啶三氟甲磺酸吡啶酯转化为N，N-二甲基氨基吡啶。在微波辐射下反应被加速。已经提出了一种新颖的一锅法，用于从可商购的氨基吡啶合成2-和4-（二甲基氨基）吡啶。该方法提供了目标产物的高收率，并且可以被认为是已知的N，N合成方法的替代方法。-二甲基吡啶-4-胺（DMAP）广泛用作有机合成中的基础催化剂。
• Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions
  作者：Pufan Ni、Lei Yang、Yi Shen、Lei Zhang、Yueyue Ma、Maolin Sun、Ruihua Cheng、Jinxing Ye

  DOI：10.1021/acs.joc.2c01133

  日期：2022.10.7

  A general method for the synthesis of phenols from electron-deficient aryl ammonium salts or heteroaryl ammonium salts under mild conditions was developed. Benzaldehyde oxime, acetohydroxamic acid, and hydroxylamine hydrochloride were investigated as hydroxide surrogates respectively. With these hydroxide surrogates, a series of phenols were prepared in yields of 20–98%.

  开发了一种在温和条件下由缺电子芳基铵盐或杂芳基铵盐合成酚类的通用方法。苯甲醛肟、乙酰氧肟酸和盐酸羟胺分别作为氢氧化物替代物进行了研究。使用这些氢氧化物替代物，可以以 20-98% 的收率制备一系列酚类。
• Tschitschibabin; Kirssanow, Chemische Berichte, 1928, vol. 61, p. 1230
  作者：Tschitschibabin、Kirssanow

  DOI：——

  日期：——
• Bromination of some pyridine and diazine N-oxides
  作者：William W. Paudler、Misa V. Jovanovic

  DOI：10.1021/jo00155a027

  日期：1983.4
• Tschitschibabin; Knunjanz, Chemische Berichte, 1928, vol. 61, p. 430
  作者：Tschitschibabin、Knunjanz

  DOI：——

  日期：——