HRID2170389

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID31398

N-Chlorosuccinimide

C4H4ClNO2

结构：Cn1nc(NS(C)(=O)=O)c2c(Cl)ccc(-c3cc(N)cnc3[C@H](Cc3cc(F)cc(F)c3)NC(=O)OC(C)(C)C)c21

HCID90290153

未命名化合物

PRODUCTS

生成物

结构：Cn1nc(NS(C)(=O)=O)c2c(Cl)ccc(-c3cc(N)c(Cl)nc3[C@H](Cc3cc(F)cc(F)c3)NC(=O)OC(C)(C)C)c21

HCID90290154

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

CONDITIONS

反应条件

温度: 60 °C

PROCEDURE

实验过程

A solution of 49A (300 mg, 0.49 mmol) in 5 mL of acetonitrile was cooled to 0° C. and treated with NCS (0.49 mmol). The reaction was heated to 60° C. overnight. The reaction mixture was partitioned with EtOAc and aqueous saturated NaHCO3, then washed with brine. The organic layer were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to provide the title compound. MS (m/z) 641 [M+H]+.

WORKUP

后处理

customThe reaction mixture was partitioned with EtOAc and aqueous saturated NaHCO3
washwashed with brine
dry with materialThe organic layer were dried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-84e5deec1fb34e0b955167add98fb33b
来源数据集: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US09050344B2
来源说明: uspto-grants-2015_06

反应 SMILES

[NH2:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[CH:28][C:29]([Cl:41])=[C:30]3[C:34]=2[N:33]([CH3:35])[N:32]=[C:31]3[NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][CH:7]=1.C1C(=O)N([Cl:49])C(=O)C1>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[CH:28][C:29]([Cl:41])=[C:30]3[C:34]=2[N:33]([CH3:35])[N:32]=[C:31]3[NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:9][C:10]2[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=2)=[N:6][C:7]=1[Cl:49]