HRID23647

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID516892

Sodium Bicarbonate

CHNaO3

结构：CN(Cc1sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c2c1COCC[Si](C)(C)C)CC(O)c1cc2ccccc2o1

HCID22574328

未命名化合物

PRODUCTS

生成物

结构：CN(Cc1sc2c(=O)c(C(=O)NCc3ccc(Cl)cc3)cn(C)c2c1CO)CC(O)c1cc2ccccc2o1

HCID22574408

未命名化合物

收率 78.7%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6212

Chloroform

CHCl3

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID6422

未命名化合物

PROCEDURE

实验过程

A solution of 154 mg of 2-{[[2-(1-benzofuran-2-yl)-2-hydroxyethyl](methyl)amino]methyl}-N-(4-chlorobenzyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide in 3 mL of 75% TFA in CH2Cl2 is stirred at room temperature for 4 h, then diluted with CHCl3 and added to stirred aq. NaHCO3. The aqueous phase is extracted with 4 portions of CH2Cl2, and the combined organic phases dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica gel using 4% MeOH in CH2Cl2 provides 103 mg of the title compound as a pale yellow solid. Recrystallization from acetonitrile affords white needles.

WORKUP

后处理

additionadded
extractionThe aqueous phase is extracted with 4 portions of CH2Cl2
dry with materialthe combined organic phases dried (Na2SO4)
concentrationconcentrated under reduced pressure

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-89fbb84a9e0d4acea2bc7a58057f2492
来源数据集: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06852731B2
来源说明: uspto-grants-2005_02

反应 SMILES

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