(R){3-[2-(4-Bromophenyl)-1-(3,5-dichlorophenylcarbamoyl)-1-methyl-ethyl]-ureido}-acetic acid ethyl ester | 397329-86-1

• 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: (R){3-[2-(4-Bromophenyl)-1-(3,5-dichlorophenylcarbamoyl)-1-methyl-ethyl]-ureido}-acetic acid ethyl ester
• 英文别名: ethyl 2-[[(2R)-3-(4-bromophenyl)-1-(3,5-dichloroanilino)-2-methyl-1-oxopropan-2-yl]carbamoylamino]acetate
• CAS: 397329-86-1
• 化学式: C₂₁H₂₂BrCl₂N₃O₄
• 分子量: 531.233
• InChiKey: QMKCYUJIGJPXBC-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R){3-[2-(4-Bromophenyl)-1-(3,5-dichlorophenylcarbamoyl)-1-methyl-ethyl]-ureido}-acetic acid ethyl ester 在 四氯化碳 、 碘代三甲硅烷 、 三甲基铝 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三苯基膦 、 三苯基氧化膦 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 57.5h， 生成 (R)-3-(4-bromobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-1H-imidazo[1,2-α]imidazol-2-one
  参考文献：
  名称：

  Development of a Scalable Process for 1-(3,5-Dichlorophenyl)-5-iodo-3-methyl- (4-methylbenzyl)-1H-imidazo[1,2-a]imidazol-2-one:  A Key Intermediate for the Synthesis of LFA-1 Inhibitors

  摘要：

  A safe, robust, chromatography-free and reproducible process for the multi-kilogram synthesis of vinyl iodide 2, a key intermediate for the synthesis of LFA-1 inhibitors, was developed and implemented at the pilot plant. Execution of the above process allowed us to support preclinical activities in the LFA-1 program.

  DOI：

  10.1021/op049813o
• 作为产物：
  描述：

  (2R)-2-amino-3-(4-bromophenyl)-N-(3,5-dichlorophenyl)-2-methyl-propionamide 、 异氰酰乙酸乙酯 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (R){3-[2-(4-Bromophenyl)-1-(3,5-dichlorophenylcarbamoyl)-1-methyl-ethyl]-ureido}-acetic acid ethyl ester
  参考文献：
  名称：

  Development of a Scalable Process for 1-(3,5-Dichlorophenyl)-5-iodo-3-methyl- (4-methylbenzyl)-1H-imidazo[1,2-a]imidazol-2-one:  A Key Intermediate for the Synthesis of LFA-1 Inhibitors

  摘要：

  A safe, robust, chromatography-free and reproducible process for the multi-kilogram synthesis of vinyl iodide 2, a key intermediate for the synthesis of LFA-1 inhibitors, was developed and implemented at the pilot plant. Execution of the above process allowed us to support preclinical activities in the LFA-1 program.

  DOI：

  10.1021/op049813o

文献信息

• Synthesis of (R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-1-H-imidazo[1,2-a]imidazol-2-one
  申请人：——

  公开号：US20020028949A1

  公开（公告）日：2002-03-07

  A novel process for the preparation of (R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-1-H-imidazo[1,2-&agr;]imidazol-2-one (1): 1 This compound is useful as an intermediate in the preparation of certain small molecules that are useful in the treatment of prevention of inflammatory and immune cell-mediated diseases. The present invention also relates to certain intermediates used in this novel process.

  一种新的制备(R)-3-(4-溴苯基)-1-(3,5-二氯苯基)-5-碘-3-甲基-1H-咪唑[1,2-a]咪唑-2-酮(1)的方法：该化合物在制备某些小分子用于治疗和预防炎症和免疫细胞介导疾病的过程中作为中间体有用。本发明还涉及在这种新的过程中使用的某些中间体。
• Regiocontrolled synthesis of highly-functionalized fused imidazoles: a novel synthesis of second generation LFA-1 inhibitors
  作者：Rogelio P. Frutos、Michael Johnson

  DOI：10.1016/s0040-4039(03)01535-1

  日期：2003.8

  A new and reliable route to a new class of LFA-1 inhibitors such as (2) has been developed. A key aspect of this route is the transformation of amino amide 5 into iodide 3 in four steps. Iodide 3 is a key advanced intermediate used in the synthesis of all second-generation 1H-imidazo[1,2-alpha]imidazol-2-one LFA-1 inhibitors. (C) 2003 Elsevier Ltd. All rights reserved.
• US6437148B1
  申请人：——

  公开号：US6437148B1

  公开（公告）日：2002-08-20
• US6441183B1
  申请人：——

  公开号：US6441183B1

  公开（公告）日：2002-08-27
• US6433183B1
  申请人：——

  公开号：US6433183B1

  公开（公告）日：2002-08-13