HRID1959384

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11667

Ethanesulfonyl chloride

C2H5ClO2S

HCID81531

Diisopropylethylamine

C8H19N

结构：CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1ncc(N2CCNCC2)nc1C#C[Si](C)(C)C

HCID66744546

未命名化合物

PRODUCTS

生成物

结构：CCS(=O)(=O)N1CCN(c2cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C#C[Si](C)(C)C)n2)CC1

HCID66745624

未命名化合物

收率 109.3%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

Ethanesulfonyl chloride (147.0 mg, 108.3 μL, 1.143 mmol) was added slowly to a stirred solution of tert-butyl N-tert-butoxycarbonyl-5-(piperazin-1-yl)-3-((trimethylsilyl)ethynyl)pyrazin-2-ylcarbamate (494 mg, 1.039 mmol) and DIPEA (161.2 mg, 217.3 μL, 1.247 mmol) in DMF (5 mL) at ambient temperature. The reaction was allowed to stir for 5 minutes and then partitioned between EtOAc/water. The aqueous layer was extracted with EtOAc (3×) and the combined organics washed with brine, dried (MgSO4), filtered and concentrated to give the product as a terracotta oil (645 mg, quantitative yield). MS (ES+) 590.05

WORKUP

后处理

custompartitioned between EtOAc/water
extractionThe aqueous layer was extracted with EtOAc (3×)
washthe combined organics washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-666c29755a78445ca37d103c6af8676b
来源数据集: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08410112B2
来源说明: uspto-grants-2013_04

反应 SMILES

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