HRID512514

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID145742

L-Proline

C5H9NO2

HCID23706191

未命名化合物

结构：CNC(=O)c1cn(Cc2ccc(C#N)cc2Br)c(C)c(-c2cccc(C(F)(F)F)c2)c1=O

HCID86711559

未命名化合物

PRODUCTS

生成物

结构：CCCS(=O)(=O)c1cc(C#N)ccc1Cn1cc(C(=O)NC)c(=O)c(-c2cccc(C(F)(F)F)c2)c1C

HCID86711558

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID24350

Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)

CuI

溶剂HCID679

Dimethyl sulfoxide

C2H6OS

CONDITIONS

反应条件

温度: 110 °C

PROCEDURE

实验过程

A mixture of preparation 25a (70 mg, 139 μmol), sodium 1-propylsulfinate (54 mg, 415 μmol), L-proline (20 mg, 174 μmol), CuI (7 mg, 37 μmol), K2CO3 (24 mg, 174 μmol) in DMSO (0.7 mL) is heated 60 min at 110° C. The reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 11 mg (15% of theory); ESI mass spectrum: [M+H]+=532; Retention time HPLC: 1.06 min (Z003—001).

WORKUP

后处理

customThe reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
custom1.06 min (Z003—001)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-92cbf3b37c1f47b6830f4878d6dca008
来源数据集: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09102624B2
来源说明: uspto-grants-2015_08

反应 SMILES

[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:8]([CH3:22])[N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=2Br)[CH:6]=1)=[O:4].[CH2:33]([S:36]([O-:38])=[O:37])[CH2:34][CH3:35].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[CH3:1][NH:2][C:3]([C:5]1[C:10](=[O:11])[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:8]([CH3:22])[N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=2[S:36]([CH2:33][CH2:34][CH3:35])(=[O:38])=[O:37])[CH:6]=1)=[O:4]