N-allyl-2-methoxyacetamide | 486393-59-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-allyl-2-methoxyacetamide
• 英文别名: N-allyl-2-methoxy-acetamide；2-methoxy-N-prop-2-enylacetamide
• CAS: 486393-59-3
• 化学式: C₆H₁₁NO₂
• mdl: MFCD19159628
• 分子量: 129.159
• InChiKey: NEICLNQEQYIEGK-UHFFFAOYSA-N

物化性质

• 沸点：
  245.3±33.0 °C(Predicted)
• 密度：
  0.956±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-iodoquinazolin-4-yl)-[3-methyl-4-(6-methylpyridin-3-yloxy)phenyl]amine hydrochloride 、 N-allyl-2-methoxyacetamide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 、 三乙胺 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 6.0h， 生成 E-2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-allyl)-acetamide dimesylate
  参考文献：
  名称：

  Evaluation of Kilogram-Scale Sonagashira, Suzuki, and Heck Coupling Routes to Oncology Candidate CP-724,714

  摘要：

  The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.

  DOI：

  10.1021/op050039u
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 N-allyl-2-methoxyacetamide
  参考文献：
  名称：

  WO2006/129168

  摘要：

  公开号：

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF N-((((PYRIDINYLOXY) -PHENYLAMINO) QUINAZOLINYL)- ALLYL) ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS WELL AS INTERMEDIATES OF SUCH PROCESSES AND PROCESSES FOR THE PREPARATION OF SUCH INTERMEDIATES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE N-((((PYRIDINYLOXY) -PHENYLAMINO) QUINAZOLINYL)- ALLYL) ACETAMIDE ET DES COMPOSES APPARENTES ET INTERMEDIAIRES POUR CES PROCEDES ET PROCEDES DE PREPARATION DE CES INTERMEDIAIRES
  申请人：PFIZER PROD INC

  公开号：WO2004089934A1

  公开（公告）日：2004-10-21

  The invention relates to processes for preparing compounds of the formula (1) and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R1, R3, R4, R6 R11, R13 R14 R15, R16, R17, k, I, and m are as defined herein. The present invention also relates to intermediates represented by the formula (3a) wherin R4, and R5 are independently selected from hydrogen and C1-C6 alkyl; each R13, R14, R15 and R16 is independently selected from hydrogen, C1-C6 alkyl and CH2OH, R17 and R18 are independently C1-C6 alkyl, and k and I are independently an integer from 1 to 3, as well as to a process for preparing these intermediates.

  本发明涉及制备式（1）化合物的方法，以及其药学上可接受的盐、前药和溶剂化物，其中R1、R3、R4、R6、R11、R13、R14、R15、R16、R17、k、I和m的定义如本文所述。本发明还涉及由式（3a）表示的中间体，其中R4和R5分别独立地选择氢和C1-C6烷基；每个R13、R14、R15和R16独立地选择氢、C1-C6烷基和CH2OH，R17和R18分别独立地选择C1-C6烷基，k和I独立地选择1至3之间的整数，以及制备这些中间体的方法。
• Processes for the preparation of substituted bicyclic derivatives for the treatment of abnormal cell growth
  申请人：Pfizer Inc.

  公开号：US20030144506A1

  公开（公告）日：2003-07-31

  The invention relates to processes for preparing compounds of the formula 1 1 and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R 1 , R 3 , R 4 , R 5 , R 11 , m and p are as defined herein. The compounds of formula 1 are useful in treating abnormal cell growth in mammals by administering pharmaceutical compositions.

  本发明涉及制备式11化合物的过程，以及其药学上可接受的盐、前药和溶剂化物，其中R1、R3、R4、R5、R11、m和p的定义如本文所述。式1化合物在哺乳动物中通过给予药物组成物来治疗异常细胞生长。
• A New Convenient Method for the Preparation of Enamides from<i>N</i>-Allylamides
  作者：Manfred Hesse、Sergey Sergeyev

  DOI：10.1055/s-2002-32962

  日期：——

  Isomerization of various N-allylamides in the presence of Fe(CO)5 smoothly afforded the corresponding enamides in yields up to 95%. The reported procedure is compatible with various functional groups including protected amino and hydroxy groups. The possible mechanism of transformation is discussed.

  在Fe(CO)5存在下，各种N-烯丙基酰胺的异构化顺利地获得了相应的烯丙基酰胺，收率高达95%。所报道的方法适用于各种官能团，包括保护氨基和羟基。讨论了可能的转化机理。
• [EN] PROCESSES FOR THE PREPARATION OF SUBSTITUTED BICYCLIC DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH<br/>[FR] PROCEDES DE PREPARATION DE DERIVES BICYCLIQUES SUBSTITUES UTILISE POUR TRAITER LA CROISSANCE CELLULAIRE ANORMALE
  申请人：PFIZER PROD INC

  公开号：WO2003045939A1

  公开（公告）日：2003-06-05

  The invention relates to processes for preparing compounds of formula (1) and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R?1, R3, R4, R5, R11¿, m and p are as defined herein. The compounds of formula (1) are useful in treating abnormal cell growth in mammals by administering pharmaceutical compositions.

  本发明涉及制备式（1）化合物的过程，以及其药学上可接受的盐、前药和溶剂化物，其中R?1、R3、R4、R5、R11、m和p如本文所定义。式（1）化合物可通过给哺乳动物施用药物组成物来治疗异常细胞生长。
• Processes for the preparation of substituted bicyclic derivatives
  申请人：Ripin H. B. David

  公开号：US20050026940A1

  公开（公告）日：2005-02-03

  The invention relates to processes for preparing compounds of the formula 1 and to pharmaceutically acceptable salts, prodrugs and solvates thereof, wherein R 1 , R 3 , R 4 , R 6 , R 11 , R 13 , R 14 , R 15 , R 16 , R 17 , k, l, and m are as defined herein. The compounds of formula 1 are useful intermediates toward preparing compounds that may be used in treating abnormal cell growth in mammals by administering pharmaceutical compositions.

  本发明涉及制备式1化合物的过程，以及其药学上可接受的盐、前药和溶剂化物，其中R1、R3、R4、R6、R11、R13、R14、R15、R16、R17、k、l和m的定义如本文所述。式1化合物是制备可用于治疗哺乳动物异常细胞生长的化合物的有用中间体，通过给药药物组合物。