HRID1033817

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID81531

Diisopropylethylamine

C8H19N

HCID13591069

3,4-Dihydroquinoline-1(2H)-carbonyl chloride

C10H10ClNO

结构：CCCCCNCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1

HCID19024425

未命名化合物

PRODUCTS

生成物

结构：CCCCCN(Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1)C(=O)N1CCCc2ccccc21

HCID19024435

未命名化合物

收率 27%

PROCEDURE

实验过程

Following the procedure of Example 7, Step B, 1,2,3,4-tetrahydroquinoline-1-carbonyl chloride (from Step A) was reacted with 1.2 equivalents of N-pentyl-N-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]amine (from Step D) in the presence of N,N-diisopropylethylamine. Flash chromatography of the crude product on silica gel (elution with 4:1 and then 3:1 hexane-EtOAc) gave two major products. (Concentration of fractions containing the pure second product afforded a 27% yield of the title compound as a stiff foam, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 723 (M+1)+. The 1H NMR spectrum indicated the presence of two isomeric forms.

WORKUP

后处理

washFlash chromatography of the crude product on silica gel (elution with 4:1
custom3:1 hexane-EtOAc) gave two major products
addition(Concentration of fractions containing the pure second product

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-2f4b341ea6dc4738acee2f571c175677
来源数据集: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05312820
来源说明: uspto-grants-1994_05

反应 SMILES

[N:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:14]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:36]=[N:35][N:34]=2)=[CH:23][CH:22]=1)[CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)C(C)C)(C)C>>[CH2:14]([N:19]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[N:37]([C:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:36]=[N:35][N:34]=2)=[CH:25][CH:26]=1)[C:11]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)=[O:12])[CH2:15][CH2:16][CH2:17][CH3:18]