HRID2293

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID24758

Sodium hydride

HNa

HCID3090641

2-(4-acetylphenoxy)ethanol

C10H12O3

结构：COc1ccccc1Oc1c(Cl)nc(-c2ncccn2)nc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1

HCID11135160

4-tert-Butyl-N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]benzene-1-sulfonamide

C25H24ClN5O4S

PRODUCTS

生成物

结构：COc1ccccc1Oc1c(NS(=O)(=O)c2ccc(C(C)(C)C)cc2)nc(-c2ncccn2)nc1OCCOc1ccc(C(C)=O)cc1

HCID67695880

未命名化合物

收率 36.1%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31374

Dimethylacetamide

C4H9NO

PROCEDURE

实验过程

To a solution of N-{6-chloro-2-(2-pyrimidyl)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (1.05 g) and 2-(4-acetylphenoxy)ethanol (728 mg) in dimethylacetamide (12 ml) is added sodium hydride (240 mg) under ice-cooling, and the mixture is stirred at room temperature overnight. The reaction solution is acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The extract is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/acetonitrile=2:1), and recrystallized from ethyl acetate/n-hexane to give N-[6-{2-(4-acetylphenoxy)ethoxy}-2-(2-pyrimidyl)-5-(2-methoxyphenoxy)pyrimidin-4-yl}-4-tert-butylbenzenesulfonamide (482 mg) as crystals.

WORKUP

后处理

temperaturecooling
extractionextracted with ethyl acetate
washThe extract is washed
customdried
customevaporated
customto remove the solvent
customThe residue is purified by silica gel column chromatography (solvent; chloroform/acetonitrile=2:1)
customrecrystallized from ethyl acetate/n-hexane

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-05c8185b891646e0a16d36d0fe17f2e9
来源数据集: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05728706
来源说明: uspto-grants-1998_03

反应 SMILES

Cl[C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:3]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36].[C:37]([C:40]1[CH:49]=[CH:48][C:43]([O:44][CH2:45][CH2:46][OH:47])=[CH:42][CH:41]=1)(=[O:39])[CH3:38].[H-].[Na+].Cl>CC(N(C)C)=O>[C:37]([C:40]1[CH:49]=[CH:48][C:43]([O:44][CH2:45][CH2:46][O:47][C:2]2[N:7]=[C:6]([C:8]3[N:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[N:5]=[C:4]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:3]=2[O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[CH:42][CH:41]=1)(=[O:39])[CH3:38]