HRID1473616

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID222

Ammonia gas

H3N

结构：CCOC(=O)COc1cc(F)ccc1-c1nccc2cc(S(=O)(=O)N(Cc3ccc(OC)cc3)c3nccs3)ccc12

HCID86687682

未命名化合物

PRODUCTS

生成物

结构：COc1ccc(CN(c2nccs2)S(=O)(=O)c2ccc3c(-c4ccc(F)cc4OCC(N)=O)nccc3c2)cc1

HCID86687683

未命名化合物

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

Ethyl 2-(5-fluoro-2-(6-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetate was dissolved in methanolic ammonia and heated at 60° C. for 16 h in a sealed tube. The reaction mixture was concentrated to obtain 2-(5-fluoro-2-(6-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetamide as light yellow solid. m/z (ESI) 579.2 (M+H)+. This was then dissolved in DCM (1 mL) and 4 drops of TFA were added and the reaction was stirred for 15 min. The reaction mixture was loaded on 10 g silica gel column and eluted with DCM:MeOH (90:10) up to 100% to obtain 2-(5-fluoro-2-(6-(N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)phenoxy)acetamide (3.9 mg, 8.51 μmol, 2.96% yield) as light yellow solid. m/z (ESI) 459.0 (M+H)+.

WORKUP

后处理

concentrationThe reaction mixture was concentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-80c689795c4e4d9e8b6b046a214b2050
来源数据集: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09012443B2
来源说明: uspto-grants-2015_04

反应 SMILES

[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25](=[O:42])(=[O:41])[N:26]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[C:27]4[S:28][CH:29]=[CH:30][N:31]=4)=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11]CC)=O.[NH3:43]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([S:25](=[O:42])(=[O:41])[N:26]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[C:27]4[S:28][CH:29]=[CH:30][N:31]=4)=[CH:22][CH:23]=3)[CH:18]=[CH:17][N:16]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([NH2:43])=[O:11]