2-乙烯吡啶分子量标准品 → (E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9503

反应方程式

HRID 9503 反应方程式
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[CH2:31].Br[C:39]1[CH:40]=[CH:41][C:42]2[C:43]3[N:52]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:51]([CH2:58][O:59][CH2:60][CH3:61])=[N:50][C:44]=3[C:45]([NH2:49])=[N:46][C:47]=2[CH:48]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:60]([O:59][CH2:58][C:51]1[N:52]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:43]2[C:42]3[CH:41]=[CH:40][C:39](/[CH:31]=[CH:30]/[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=4)=[CH:48][C:47]=3[N:46]=[C:45]([NH2:49])[C:44]=2[N:50]=1)[CH3:61]

参与物

7

反应物 4

HCID 75212-乙烯吡啶分子量标准品HCID 8471三乙胺HCID 80271三(邻甲基苯基)磷HCID 219840707-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

产物 1

HCID 21984053(E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 1140甲苯溶剂

反应条件

温度
120 °C

实验过程

A thick walled glass tube, equipped with magnetic stir-bar, was charged with toluene (20 mL/g), palladium (II) acetate (0.1 equivalents), tri-ortho-tolylphosphine (0.3 equivalents), triethylamine (3.0 equivalents), 2-vinylpyridine (1.0 equivalent), and 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 eq.). The tube was purged with nitrogen and sealed. The reaction mixture was heated at 120° C. for 24–48 hours. The reaction mixture was allowed to cool and then concentrated under reduced pressure. The solid residue was partitioned between dichloromethane and water, and the mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide. The organic layer was separated and purified by flash chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile to provide (E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

后处理

  1. customA thick walled glass tube, equipped with magnetic stir-bar
  2. customThe tube was purged with nitrogen
  3. customsealed
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. customThe solid residue was partitioned between dichloromethane and water
  7. additionthe mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide
  8. customThe organic layer was separated
  9. custompurified by flash chromatography on silica gel (
  10. washeluting with chloroform
  11. custommethanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

来源与证据

ORD记录
ord-02f3772b166949dc9620d2ef20591eba
来源数据集
uspto-grants-2006_08
专利号
US07091214B2

关联笔记

加载中…