化工社
首页MCP工作台Skills
首页工作台通知我的
llms.txt · MCP 指南隐私政策 · 服务条款 · 支持v1.8.0
  1. 首页
  2. /反应

ubiquitin cross-reactive protein → 1,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxylate

HRID 1874792
笔记
打印预览

反应方程式

HRID 1874792 反应方程式
CO[C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[CH2:8][CH2:9][NH:10][C:11](=[O:23])[C:12]=3[N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:27][C:28]1[C:29]([F:45])=[C:30]([O:35][C:36]2[CH:37]=[C:38]([CH:41]=[C:42]([Cl:44])[CH:43]=2)[C:39]#[N:40])[C:31]([Cl:34])=[CH:32][CH:33]=1.C(O)(=O)C[C:48](CC(O)=O)(C(O)=O)[OH:49]>C1COCC1.CCOC(C)=O>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:10]2[CH2:9][CH2:8][C:7]3[C:6]4[C:14](=[CH:15][CH:3]=[C:4]([O:49][CH3:48])[CH:5]=4)[N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[C:12]=3[C:11]2=[O:23])=[C:29]([F:45])[C:30]=1[O:35][C:36]1[CH:37]=[C:38]([C:39]#[N:40])[CH:41]=[C:42]([Cl:44])[CH:43]=1
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

7

反应物 4

HCID 311ubiquitin cross-reactive proteinHCID 24758氢化钠HCID 594515763-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 709371861,1-Dimethylethyl 7-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxylate

产物 1

HCID 594515721,1-Dimethylethyl 2-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-beta-carboline-9-carboxylate
收率 24%

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
0 °C

实验过程

1,1-Dimethylethyl 7-(methyloxy)-1-oxo-1,2,3,4-tetrahydro-9H-β-carboline-9-carboxylate (0.075 g, 0.23 mmol) was dissolved in THF (2 mL) and cooled to 0° C. Sodium hydride (60% dispersion in oil, 0.01 g, 0.25 mmol) was added and the mixture was stirred for 15 min. 3-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.09 g, 0.23 mmol) was added. The reaction mixture was allowed to warm to RT and stirred for 1 h. 10% Aqueous citric acid and EtOAc were added. The layers were separated and the aqueous layer extracted with EtOAc (3×5 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (0.034 g, 24%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.83 (s, 1H), 7.81 (d, 1H), 7.52 (d, 1H), 7.45-7.51 (m, 2H), 7.34 (t, 1H), 7.20 (d, 1H), 7.07 (dd, 1H), 4.79 (s, 2H), 3.79 (s, 3H), 3.71 (t, 2H), 2.94 (t, 2H), 1.48 (s, 9H). MS: m/z 632.2 (M+23).

后处理

  1. temperatureto warm to RT
  2. stirringstirred for 1 h
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (3×5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification

来源与证据

ORD记录
ord-62a8d91dc3e2483c854836804c758a77
来源数据集
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08304419B2

反应笔记

加载中…

本页导航参与物反应条件实验过程后处理来源与证据反应笔记