HRID13428

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID123350

4-(Methylsulfonyl)phenol

C7H8O3S

结构：CC(=O)N1CC(C)CC1c1cc([N+](=O)[O-])c(NC(=O)c2ccccn2)cc1F

HCID23145536

未命名化合物

HCID85782573

未命名化合物

PRODUCTS

生成物

结构：CC(=O)N1CC(C)CC1c1cc2[nH]c(-c3ccccn3)nc2cc1Oc1ccc(S(C)(=O)=O)cc1

HCID23145296

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

溶剂HCID13387

N-Methyl-2-pyrrolidone

C5H9NO

CONDITIONS

反应条件

温度: 90 °C

PROCEDURE

实验过程

13.4 mg of 4-(methanesulfonyl)phenol and 44.9 mg of cesium carbonate were added in order to an N-methyl-pyrrolidinone (2 ml) solution of 15 mg of N-(4-(1-acetyl-4-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at 90° C. for 1 hour. 43.8 mg of tin chloride dihydrate was added to the reaction liquid, then heated up to 100° C. and stirred for 2 hours. The reaction liquid was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1) to obtain the entitled compound as a white solid.

WORKUP

后处理

customthe reaction liquid
temperatureheated up to 100° C.
stirringstirred for 2 hours
customThe reaction liquid
washwashed with aqueous saturated sodium bicarbonate
dry with materialdried with anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified
customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=9/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-19d0527dd4c44853b78367b7e8838554
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07728025B2
来源说明: uspto-grants-2010_06

反应 SMILES

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([N:21]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]1[C:27]1[C:32](F)=[CH:31][C:30]([NH:34][C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=O)=[C:29]([N+:43]([O-])=O)[CH:28]=1)(=[O:20])[CH3:19].O.O.[Sn](Cl)(Cl)(Cl)Cl>C(OCC)(=O)C.CN1CCCC1=O>[C:18]([N:21]1[CH2:25][CH:24]([CH3:26])[CH2:23][CH:22]1[C:27]1[C:32]([O:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:31][C:30]2[N:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[NH:43][C:29]=2[CH:28]=1)(=[O:20])[CH3:19]