HRID18568

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID4067207

3-Methoxybenzyl bromide

C8H9BrO

HCID18373917

Acetonitrile--water (1/1)

C2H5NO

结构：COC(=O)c1ccc2[nH]c(C(=O)NC3CCN(C(C)C)CC3)nc2c1

HCID178497373

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc2c(c1)nc(C(=O)NC1CCN(C(C)C)CC1)n2Cc1cccc(OC)c1

HCID67012585

未命名化合物

结构：COC(=O)c1ccc2nc(C(=O)NC3CCN(C(C)C)CC3)n(Cc3cccc(OC)c3)c2c1

HCID67013116

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID284

Formic acid

CH2O2

PROCEDURE

实验过程

2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid methyl ester and 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-3-(3-methoxy-benyl)-3H-benzoimidazole-5-carboxylic acid methyl ester were prepared by a procedure according to example 5 iii) starting from 300 mg (0.87 mmol) 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic acid methyl ester and 210.2 mg (1.04 mmol) 1-bromomethyl-3-methoxy-benzene. Preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave a 1:1 mixture of both isomers described in the title. These isomers could be separated by NP-HPLC using a chiral stationary phase and a mixture of heptane, ethanol, methanol and diethyl amine as solvent. Structural assignment of both isomers was achieved by NOE-spectroscopy.

WORKUP

后处理

additiona 1:1 mixture of both isomers
customThese isomers could be separated by NP-HPLC
additiona mixture of heptane, ethanol, methanol and diethyl amine as solvent

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-46c1df599af045bebf0a7d91947851a4
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07741341B2
来源说明: uspto-grants-2010_06

反应 SMILES

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