HRID1446536

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6228

N,N-Dimethylformamide

C3H7NO

HCID88198

p-tert-Butylbenzyl chloride

C11H15Cl

HCID2733832

Lithium Hexamethyldisilazide

C6H18LiNSi2

$结构：COc1cc(/C=C2\CCCNC2=O)ccc1-n1cnc(C)c1$

HCID58548909

未命名化合物

PRODUCTS

生成物

$结构：COc1cc(/C=C2\CCCN(Cc3ccc(C(C)(C)C)cc3)C2=O)ccc1-n1cnc(C)c1$

HCID11690815

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a DMF (2 mL) solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one (70 mg) obtained in Example 416, lithium bis(trimethylsilyl)amide (1M THF solution, 0.47 mL) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes under ice-cooling. Subsequently, 1-tert-butyl-4-chloromethylbenzene (0.073 mL) was added to the reaction solution, and the reaction solution was agitated for 30 minutes under ice-cooling. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The obtained organic layer was dried with magnesium sulfate and was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system), and 37.8 mg of the title compound was obtained. The physical properties are as follows.

WORKUP

后处理

temperaturecooling
temperaturecooling
stirringthe reaction solution was agitated for 30 minutes under ice-
temperaturecooling
customthe organic layer was partitioned
dry with materialThe obtained organic layer was dried with magnesium sulfate
concentrationwas concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cb365548c5814d399ec9b78914197dd9
来源数据集: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07667041B2
来源说明: uspto-grants-2010_02

反应 SMILES

CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1)/[CH:11]=[C:12]1/[C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH2:17]/1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:38]([C:42]1[CH:47]=[CH:46][C:45]([CH2:48]Cl)=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39]>C(OCC)(=O)C.O>[C:38]([C:42]1[CH:43]=[CH:44][C:45]([CH2:48][N:14]2[CH2:15][CH2:16][CH2:17]/[C:12](=[CH:11]\[C:10]3[CH:19]=[CH:20][C:21]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:8]([O:7][CH3:6])[CH:9]=3)/[C:13]2=[O:18])=[CH:46][CH:47]=1)([CH3:41])([CH3:39])[CH3:40]