HRID551134

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID85247

Silane, iodotrimethyl-

C3H9ISi

HCID611195

4-tert-Butylphenoxyacetyl chloride

C12H15ClO2

结构：Cc1ccc(-c2cccc(C(N)Cc3cc(Cl)c4cccnc4c3OCc3ccccc3)c2)s1

HCID67171449

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2cccc(C(Cc3cc(Cl)c4cccnc4c3O)NC(=O)COc3ccc(C(C)(C)C)cc3)c2)s1

HCID59829695

未命名化合物

收率 126.6%

结构：Cc1ccc(-c2cccc(C(Cc3cc(Cl)c4cccnc4c3OCc3ccccc3)NC(=O)COc3ccc(C(C)(C)C)cc3)c2)s1

HCID67171827

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-tert-butyl-phenoxy)-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.414 mmol) and 4-tert-butyl-phenoxyacetyl chloride (0.455 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). Ethyl acetate was used in place of dichloromethane in the workup procedure. Crude product obtained was a white solid that was subjected to the conditions described above for TMSI-mediated O-benzyl deprotection Crude product obtained was a brown solid that was purified by column chromatography using 5% methanol/dichloromethane to give the title compound as a white solid (0.262 mmol, 64% for 2 steps). MS (ESI) m/z 585.4.

WORKUP

后处理

customCrude product obtained
customobtained
customwas purified by column chromatography

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b8e803d0fa9e4a21a509e24b2507dc6e
来源数据集: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07947712B2
来源说明: uspto-grants-2011_05

反应 SMILES

[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[NH2:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45](Cl)=[O:46])=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36].[Si](I)(C)(C)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([NH:22][C:45](=[O:46])[CH2:44][O:43][C:42]2[CH:48]=[CH:49][C:39]([C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:40][CH:41]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([C:39]1[CH:49]=[CH:48][C:42]([O:43][CH2:44][C:45]([NH:22][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[CH2:20][C:10]2[C:9]([OH:8])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([Cl:19])[CH:11]=2)=[O:46])=[CH:41][CH:40]=1)([CH3:38])([CH3:36])[CH3:37]