6-(5-Chloro-4-cyano-3-difluoromethyl-pyrazol-1-yl)-pyridine-3-sulfonic acid amide carbonitrile | 521085-24-5

• 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: 6-(5-Chloro-4-cyano-3-difluoromethyl-pyrazol-1-yl)-pyridine-3-sulfonic acid amide carbonitrile
• 英文别名: 6-[5-Chloro-4-cyano-3-(difluoromethyl)pyrazol-1-yl]pyridine-3-sulfonamide
• CAS: 521085-24-5
• 化学式: C₁₀H₆ClF₂N₅O₂S
• 分子量: 333.706
• InChiKey: AXSWUVRXYVPPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(5-Chloro-4-cyano-3-difluoromethyl-pyrazol-1-yl)-pyridine-3-sulfonic acid amide carbonitrile 、 3-甲基哌啶 在 potassium fluoride 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到6-[4-Cyano-3-(difluoromethyl)-5-(3-methylpiperidin-1-yl)pyrazol-1-yl]pyridine-3-sulfonamide
  参考文献：
  名称：

  氟介导的5-烷基氨基和醚取代吡唑的高效合成

  摘要：

  1-（4-甲基磺酰基（或磺酰胺基）-2-吡啶基）-5-氯-4-氰基吡唑与各种胺和醇的氟化物介导的亲核取代反应在温和条件下发生，以提供5-烷基氨基和醚吡唑中等至高产。

  DOI：

  10.1016/j.tetlet.2005.08.022
• 作为产物：
  描述：

  6-(3-Difluoromethyl-5-hydroxy-pyrazol-1-yl)-pyridine-3-sulfonic acid amide 在 盐酸 、 2,2,2-三氟乙醇 、 盐酸羟胺 、 三乙胺 、 三氯乙酰氯 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 6-(5-Chloro-4-cyano-3-difluoromethyl-pyrazol-1-yl)-pyridine-3-sulfonic acid amide carbonitrile
  参考文献：
  名称：

  5-Heteroatom substituted pyrazoles as canine COX-2 inhibitors. Part 1: Structure–activity relationship studies of 5-alkylamino pyrazoles and discovery of a potent, selective, and orally active analog

  摘要：

  Structure-activity relationship (SAR) studies of the novel 2-[3-di and trifluoromethyl-5-alkylamino pyrazo-1-yl]-5-methanesulfonyl (SO2Me)/sulfamoyl (SO2NH2)-pyridine derivatives for canine COX enzymes are described. The studies led to the identification of 2e as lead with potent in vitro activity, selectivity, and in vivo activity in dogs and cats. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.006

文献信息

• Efficient synthesis of 5-heteroatom-containing -pyrazoles
  申请人：——

  公开号：US20030139407A1

  公开（公告）日：2003-07-24

  An efficient synthesis of sulfonyl pyrazoles of formula I: 1 wherein the ring of the formula (R 5 )—A—(SO m R 4 ), m, R 1 through R 9 are as defined in the specification, comprising reacting a compound of formula II: 2 wherein the ring of the formula (R 5 )—A—(SO m 4 ), m R 1 through R 9 are as defined above and wherein R 10 is halo, (C 1 -C 6 )alkyl-SO 3 —, (C 6 -C 10 )aryl-SO 3 —, (C 1 -C 6 )alkyl-SO 2 —, or (C 6 -C 10 )aryl-SO 2 —; wherein each of said (C 1 -C 6 )alkyl component of said (C 1 -C 6 )alkyl-SO 3 — and (C 1 -C 6 )alkyl-SO 2 — radicals may optionally be substituted on any carbon atom by one to six fluoro substituents per (C 1 -C 6 )alkyl component; with a compound of formula R 3 —H, wherein R 3 is as defined above, in the presence of a fluoride containing salt and in the presence of a solvent.

  一种有效的合成公式I：1的磺酰吡唑，其中公式的环（R5）-A-（SOmR4），m，R1到R9如规范中所定义，包括在氟化物盐和溶剂的存在下，将公式II的化合物反应：2其中公式的环（R5）-A-（SOm4），m，R1到R9如上所定义，其中R10是卤素，（C1-C6）烷基-SO3-，（C6-C10）芳基-SO3-，（C1-C6）烷基-SO2-或（C6-C10）芳基-SO2-；其中每个（C1-C6）烷基-SO3-和（C1-C6）烷基-SO2-基团的（C1-C6）烷基组分可以选择地被每个碳原子取代一个到六个氟代基。其中R3为上述定义的化合物R3-H进行反应。
• Efficient synthesis of 5-heteroatom-containing-pyrazoles
  申请人：——

  公开号：US20040210052A1

  公开（公告）日：2004-10-21

  An efficient synthesis of sulfonyl pyrazoles of formula I: 1 wherein the ring of the formula (R 5 )—A—(SO m R 4 ), m, R 1 through R 9 are as defined in the specification, comprising reacting a compound of formula II: 2 wherein the ring of the formula (R 5 )—A—(SO m R 4 ), m R 1 through R 9 are as defined above and wherein R 10 is halo, (C 1 -C 6 )alkyl-SO 3 —, (C 6 -C 10 )aryl-SO 3 —, (C 1 -C 6 )alkyl-SO 2 —, or (C 6 -C 10 )aryl-SO 2 —; wherein each of said (C 1 -C 6 )alkyl component of said (C 1 -C 6 )alkyl-SO 3 — and (C 1 -C 6 )alkyl-SO 2 — radicals may optionally be substituted on any carbon atom by one to six fluoro substituents per (C 1 -C 6 )alkyl component; with a compound of formula R 3 —H, wherein R 3 is as defined above, in the presence of a fluoride containing salt and in the presence of a solvent.

  一种有效合成式I：1的磺酰基吡唑的方法，其中式中的环(R5)-A-(SOmR4)，m，R1至R9如规范中定义，包括在存在氟化盐和溶剂的条件下，将式II的化合物与R3-H的化合物反应，其中式中的环(R5)-A-(SOmR4)，m，R1至R9如上所述，而R10为卤素，(C1-C6)烷基-SO3-，(C6-C10)芳基-SO3-，(C1-C6)烷基-SO2-或(C6-C10)芳基-SO2-；其中所述(C1-C6)烷基-SO3-和(C1-C6)烷基-SO2-基团的每个碳原子上均可选择地被一个到六个氟取代基取代。
• AN EFFICIENT SYNTHESIS OF 5-HETEROATOM-CONTAINING-PYRAZOLES
  申请人：Pfizer Products Inc.

  公开号：EP1440062A1

  公开（公告）日：2004-07-28
• US6794512B2
  申请人：——

  公开号：US6794512B2

  公开（公告）日：2004-09-21
• [EN] AN EFFICIENT SYNTHESIS OF 5-HETEROATOM-CONTAINING-PYRAZOLES<br/>[FR] PROCEDE EFFICACE DE SYNTHESE DE PYRAZOLES CONTENANT CINQ HETEROATOMES
  申请人：PFIZER PROD INC

  公开号：WO2003037874A1

  公开（公告）日：2003-05-08

  An efficient synthesis of sulfonyl pyrazoles of formula (I), wherein the ring of the formula (R5)-A-(SO¿m?R?4), m, R1¿ through R9 are as defined in the specification, comprising reacting a compound of formula (II), wherein the ring of the formula (R5)-A-(SO¿m?R?4), m R1¿ through R9 are as defined above and wherein R10 is halo, (C¿1?-C6)alkyl-SO3-, (C6-C10)aryl-SO3-, (C1-C6)alkyl-SO2-, or (C6-C10)aryl-SO2-; wherein each of said (C1-C6)alkyl component of said (C1-C6)alkyl- SO3- and (C1-C6)alkyl-SO2- radicals may optionally be substituted on any carbon atom by one to six fluoro substituents per (C1-C6)alkyl component; with a compound of formula R?3¿-H, wherein R3 is as defined above, in the presence of a fluoride containing salt and in the presence of a solvent.