2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine trifluoroacetate salt | 1220518-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine trifluoroacetate salt
• 英文别名: 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine trifluoroacetate
• CAS: 1220518-03-5
• 化学式: C₂HF₃O₂*C₁₃H₁₃ClN₆
• 分子量: 402.763
• InChiKey: JEIISGVVUYWCSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.86
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(5-氟嘧啶-2-基)乙胺盐酸盐 、 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine trifluoroacetate salt 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 反应 3.0h， 以14%的产率得到7-cyclopropyl-N2-[1-(5-fluoropyrimidin-2-yl)ethyl]-N4-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine trifluoroacetate salt
  参考文献：
  名称：

  Discovery of 1-Methyl-1H-imidazole Derivatives as Potent Jak2 Inhibitors

  摘要：

  Structure based design, synthesis, and biological evaluation of a novel series of 1-methyl-1H-imidazole, as potent Jak2 inhibitors to modulate the Jak/STAT pathway, are described. Using the C-ring fragment from our first clinical candidate AZD1480 (24), optimization of the series led to the discovery of compound 19a, a potent, orally bioavailable Jak2 inhibitor. Compound 19a displayed a high level of cellular activity in hematopoietic cell lines harboring the V617F mutation and in murine BaF3 TEL-Jak2 cells. Compound 19a demonstrated significant tumor growth inhibition in a UKE-1 xenograft model within a well-tolerated dose range.

  DOI：

  10.1021/jm401546n
• 作为产物：
  描述：

  2,4-二氯-7H吡咯[2,3-D]嘧啶 在 吡啶 、 copper diacetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 38.0h， 生成 2-chloro-7-cyclopropyl-N-(1-methyl-1H-imidazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine trifluoroacetate salt
  参考文献：
  名称：

  Discovery of 1-Methyl-1H-imidazole Derivatives as Potent Jak2 Inhibitors

  摘要：

  Structure based design, synthesis, and biological evaluation of a novel series of 1-methyl-1H-imidazole, as potent Jak2 inhibitors to modulate the Jak/STAT pathway, are described. Using the C-ring fragment from our first clinical candidate AZD1480 (24), optimization of the series led to the discovery of compound 19a, a potent, orally bioavailable Jak2 inhibitor. Compound 19a displayed a high level of cellular activity in hematopoietic cell lines harboring the V617F mutation and in murine BaF3 TEL-Jak2 cells. Compound 19a demonstrated significant tumor growth inhibition in a UKE-1 xenograft model within a well-tolerated dose range.

  DOI：

  10.1021/jm401546n