HRID1636792

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID795

Imidazole

C3H4N2

HCID28928

Chloro(1,1-dimethylethyl)dimethylsilane

C6H15ClSi

结构：N#Cc1ccc(O)c(CN2CCC(NS(=O)(=O)c3ccc(-c4cccnc4)s3)C2=O)c1

HCID54264613

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)[Si](C)(C)Oc1ccc(C#N)cc1CN1CC[C@H](NS(=O)(=O)c2ccc(-c3cccnc3)s2)C1=O

HCID54297977

未命名化合物

收率 74.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Imidazole (0.094 g, 1.37 mol) and t-butyldimethylchlorosilane (0.099 g, 0.66 mmol) are added to a solution of 5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide (0.25 g, 0.55 mmol) in 10 mL of DMF. The resulting mixture is stirred overnight, and then diluted with EtOAc and washed with saturated NaHCO3 (aq) and brine. The organic layer is dried over MgSO4, filtered and concentrated. The product is purified by column chromatography eluting with 3% MeOH/CH2Cl2 to give a brown oil (0.236 g, 0.41 mmol).

WORKUP

后处理

washwashed with saturated NaHCO3 (aq) and brine
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe product is purified by column chromatography
washeluting with 3% MeOH/CH2Cl2

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-0fc617d8f5e94312a0140e20f268bfcd
来源数据集: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06034093
来源说明: uspto-grants-2000_03

反应 SMILES

N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([OH:44])=[C:20]([CH:43]=1)[CH2:21][N:22]1[CH2:26][CH2:25][CH:24]([NH:27][S:28]([C:31]2[S:32][C:33]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)(=[O:30])=[O:29])[C:23]1=[O:42])#[N:15]>CN(C=O)C.CCOC(C)=O>[C:6]([Si:10]([CH3:13])([CH3:12])[O:44][C:19]1[CH:18]=[CH:17][C:16]([C:14]#[N:15])=[CH:43][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([C:31]2[S:32][C:33]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)(=[O:30])=[O:29])[C:23]1=[O:42])([CH3:9])([CH3:8])[CH3:7]