HRID245236

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID78703

4-(1-Pyrrolidinyl)piperidine

C9H18N2

结构：COC(=O)c1c(CBr)c(-c2cccc(C(F)(F)F)c2)nc2ccc(S(C)(=O)=O)cc12

HCID67383823

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1c(CN2CCC(N3CCCC3)CC2)c(-c2cccc(C(F)(F)F)c2)nc2ccc(S(C)(=O)=O)cc12

HCID67419178

未命名化合物

收率 93.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

An orange suspension of methyl 3-(bromomethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.068 g, 2.126 mmol) and 4-(1-pyrrolidinyl)piperidine (0.492 g, 3.19 mmol) in acetonitrile (14.17 ml) was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was absorbed onto florisil and was purified via column chromatography (ISCO, 12 g silica, 5-10% methanol/dichloromethane) to give methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.14 g, 88% yield). MS (m/z) 576.2 (M+H+).

WORKUP

后处理

customThe solvent was removed under reduced pressure
customThe residue was absorbed onto florisil
customwas purified via column chromatography (ISCO, 12 g silica, 5-10% methanol/dichloromethane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ef170657c88b47cebaadfc95a8b37adf
来源数据集: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08658636B2
来源说明: uspto-grants-2014_02

反应 SMILES

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