5-bromo-2-methyl<3,4'-bipyridin>-6(1H)-one | 80047-33-2

• 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: 5-bromo-2-methyl<3,4'-bipyridin>-6(1H)-one
• 英文别名: 3-bromo-6-methyl-5-pyridin-4-yl-1H-pyridin-2-one
• CAS: 80047-33-2
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: HDGZAELAIYUTCS-UHFFFAOYSA-N

物化性质

• 熔点：
  252-254 °C(Solv: methanol (67-56-1))
• 沸点：
  441.2±45.0 °C(Predicted)
• 密度：
  1.547±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-methyl<3,4'-bipyridin>-6(1H)-one 在 N-甲基吡咯烷酮 、 ammonium hydroxide 、 sodium methylate 、 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 47.5h， 生成 5-methyl-6-(4-pyridinyl)thiazolo-<4,5-b>pyridin-2(3H)-one
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193
• 作为产物：
  描述：

  6-methoxy-2-methyl-3,4'-bipyridine 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 作用下， 以 甲醇 为溶剂， 反应 55.0h， 生成 5-bromo-2-methyl<3,4'-bipyridin>-6(1H)-one
  参考文献：
  名称：

  Synthesis of Milrinone, a Cardiotonic Agent

  摘要：

  DOI：

  10.3987/com-89-5276

文献信息

• 3-(Hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone
  申请人：Sterling Drug Inc.

  公开号：US04361569A1

  公开（公告）日：1982-11-30

  3-(Hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically acceptable acid-addition salt thereof is useful as a cardiotonic agent. 3-Hydroxy-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by autoclaving a mixture of a sodium or potassium lower-alkoxide, a lower-alkanol and 3-(chloro or bromo)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone and acidifying the reaction mixture. 3-Hydroxymethyl-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by reacting 6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone with excess formaldehyde at an acidic pH. Said 3-(hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically acceptable acid-addition salt thereof is disclosed as the active ingredient in cardiotonic compositions for increasing cardiac contractility and in the method for increasing cardiac contractility in a patient requiring such treatment.

  3-(羟基或羟甲基)-6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮或其药学上可接受的酸盐加成物作为一种心脏强心剂具有用途。3-羟基-6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮是通过在钠或钾的低级烷氧化物、低级醇和3-(氯或溴)-6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮的混合物中进行高压灭菌并使反应混合物酸化制备的。3-羟甲基-6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮是通过在酸性pH下使6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮与过量甲醛反应制备的。所述的3-(羟基或羟甲基)-6-甲基-5-(4-吡啶基)-2(1H)-吡啶酮或其药学上可接受的酸盐加成物被披露为心脏强心剂组合物的活性成分，用于增加心脏收缩力并用于需要该治疗的患者的增加心脏收缩力的方法。
• 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their
  申请人：Sterling Drug Inc.

  公开号：US04313951A1

  公开（公告）日：1982-02-02

  1-R.sub.1 -3-[amino, cyano, carbamyl, halo, lower-alkylamino, di-(lower-alkyl)amino or lower-acylamino]-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones or pharmaceutically-acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. 1-R.sub.1 -3-amino-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carbamyl compounds and reacting the latter with a reagent capable of converting carbamyl to amino. The 1-R.sub.1 -3-cyano-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones are prepared by reacting (pyridinylmethyl) lower-alkyl ketones with dimethylformamide di-(lower-alkyl) acetal to produce 1-(pyridinyl)-2-(dimethylamino)ethenyl lower-alkyl ketone and reacting said ketones with N-R.sub.1 -.alpha.-cyanoacetamide to produce the 1-R.sub.1 -3-cyano-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones. Also shown are the conversions: of the 3-cyano compounds to the 3-H compounds; of the 3-H compounds to the 3-halo compounds; of the 3-halo compounds to the 3-[mono-(lower-alkyl)- or di-(lower-alkyl)-amino]compounds; and, of the 3-amino compounds to the 3-lower-acylamino or 3-[mono-(lower-alkyl)- or di-(lower-alkyl)amino] compounds.

  1-R.sub.1 -3-[氨基，氰基，氨基甲酰基，卤素，较低烷基氨基，双-(较低烷基)氨基或较低酰胺基]-6-(较低烷基)-5-(吡啶基)-2(1H)-吡啶酮或其药学上可接受的酸加合物或阳离子盐作为心力衰竭药物具有用途，其中R.sub.1为氢，较低烷基或较低羟基烷基。1-R.sub.1 -3-氨基-6-(较低烷基)-5-(吡啶基)-2(1H)-吡啶酮是通过水解相应的3-氰基化合物以产生相应的3-氨基甲酰基化合物并将后者与能将氨甲酰基转化为氨基的试剂反应而制备的。1-R.sub.1 -3-氰基-6-(较低烷基)-5-(吡啶基)-2(1H)-吡啶酮是通过将(吡啶基甲基)较低烷基酮与二甲基甲酰胺双-(较低烷基)缩醛反应以产生1-(吡啶基)-2-(二甲氨基)乙烯基较低烷基酮并将该酮与N-R.sub.1-.alpha.-氰基乙酰胺反应以产生1-R.sub.1 -3-氰基-6-(较低烷基)-5-(吡啶基)-2(1H)-吡啶酮制备的。还显示了以下转化：3-氰基化合物至3-H化合物的转化；3-H化合物至3-卤素化合物的转化；3-卤素化合物至3-[单-(较低烷基)-或双-(较低烷基)-氨基]化合物的转化；以及3-氨基化合物至3-较低酰胺基或3-[单-(较低烷基)-或双-(较低烷基)氨基]化合物的转化。
• Singh; Bacon; Robinson, Journal of Medicinal Chemistry, 1994, vol. 37, # 2, p. 248 - 254
  作者：Singh、Bacon、Robinson、Fritz、Lesher、Kumar、Dority、Reuman、Kuo、Eissenstat、Pagani、Bode、Bentley、Connell、Hamel、Silver

  DOI：——

  日期：——
• SHIAO, MIN-JEN;SHYU, LI-MING;CHEN, CHIEH-FU, HETEROCYCLES, 31,(1990) N, C. 523-527
  作者：SHIAO, MIN-JEN、SHYU, LI-MING、CHEN, CHIEH-FU

  DOI：——

  日期：——
• LESHER, G. Y.;PHILION, R. E.
  作者：LESHER, G. Y.、PHILION, R. E.

  DOI：——

  日期：——