HRID1749952

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1ccc2c(c1C#CCCN1CCN(C(=O)OC(C)(C)C)CC1)OCC2=O

HCID71278868

未命名化合物

HCID178520025

未命名化合物

PRODUCTS

生成物

$结构：COc1ccc2c(c1C#CCCN1CCN(C(=O)OC(C)(C)C)CC1)O/C(=C\c1n[nH]c3ccccc13)C2=O$

HCID178487166

未命名化合物

收率 66.7%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID8082

Piperidine

C5H11N

溶剂HCID887

Methanol

CH4O

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

A solution of tert-butyl 4-[4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)but-3-ynyl]piperazine-1-carboxylate (0.0394 g, 0.0983 mmol) in methanol (3 mL) was added with 1H-indazole-3-carboxaldehyde (0.0131 g, 0.0894 mmol) and piperidine (5 drops), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl (Z)-4-(4-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}but-3-ynyl)piperazine-1-carboxylate (0.0315 g, 66%).

WORKUP

后处理

concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2766dab925034a49be4e40dd579aefdf
来源数据集: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09156827B2
来源说明: uspto-grants-2015_10

反应 SMILES

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[C:13]#[C:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[N:31]1>CO.N1CCCCC1>[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](/[CH:39]=[C:8]2\[O:9][C:5]3[C:4]([C:13]#[C:14][CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:31]1