HRID1443990

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID117640

tert-Butyl 4-hydroxybenzoate

C11H14O3

结构：COc1nc(Br)cnc1N(COCC[Si](C)(C)C)S(=O)(=O)c1cccc(Cl)c1Cl

HCID59168156

未命名化合物

PRODUCTS

生成物

结构：COc1nc(Oc2ccc(C(=O)O)cc2)cnc1NS(=O)(=O)c1cccc(Cl)c1Cl

HCID10217298

未命名化合物

HCID21882781

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

4-Hydroxybenzoic acid tert butyl ester (0.13 g), N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55 part a) (0.35 g) and caesium carbonate (0.42 g) in acetonitrile (10 mL) was heated at 50° C. After 12 h, the mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound protected with the SEM group and tert butyl group as an oil. The oil was dissolved in trifluoroacetic acid (2.0 mL) and stirred at room temperature for 3 h.

WORKUP

后处理

washwashed with water
dry with materialdried (MgSO4)
customevaporated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8d80e8d66a0540ac95b0b7753090fc66
来源数据集: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07662825B2
来源说明: uspto-grants-2010_02

反应 SMILES

[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(C)(C)[CH3:2].Br[C:16]1[N:17]=[C:18]([O:42][CH3:43])[C:19]([N:22](COCC[Si](C)(C)C)[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])(=[O:25])=[O:24])=[N:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[C:6]([O:5][CH2:1][CH3:2])(=[O:14])[CH3:7].[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[Cl:33][C:27]1[C:28]([Cl:32])=[CH:29][CH:30]=[CH:31][C:26]=1[S:23]([NH:22][C:19]1[N:20]=[CH:21][C:16]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:5])=[O:14])=[CH:12][CH:11]=2)=[N:17][C:18]=1[O:42][CH3:43])(=[O:25])=[O:24]