HRID613624

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID10654899

未命名化合物

结构：CC(=O)Nc1ccc(/C=C/C(=O)NCc2cccn2-c2ccc(Cl)c(COS(C)(=O)=O)c2Cl)cn1

HCID18321761

未命名化合物

PRODUCTS

生成物

结构：COc1nc2c(OC(C)c3c(Cl)ccc(-n4cccc4CNC(=O)/C=C/c4ccc(NC(C)=O)nc4)c3Cl)cccc2[nH]1

HCID18321861

未命名化合物

收率 23.7%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A mixture of 4-hydroxy-2-methoxy-1-methyl-1H-benzimidazole (47.4 mg), 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole (143 mg) and potassium carbonate (110 mg) in N,N-dimethylformamide (4 ml) was stirred at ambient temperature for 3.5 days. The mixture was partitioned between chloroform and water. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V) to give 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrrole (39 mg) as colorless crystals.

WORKUP

后处理

customThe mixture was partitioned between chloroform and water
dry with materialThe separated organic layer was dried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f1f8360dc65d4d72be531b5c50ccd4bc
来源数据集: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06008229
来源说明: uspto-grants-1999_12

反应 SMILES

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