HRID18553

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID3421110

2-Bromo-N-(5-chloro-2-pyridinyl)acetamide

C7H6BrClN2O

HCID18373917

Acetonitrile--water (1/1)

C2H5NO

结构：CC(C)N1CCC(NC(=O)c2nc3cc(S(=O)(=O)CCO)ccc3[nH]2)CC1

HCID178456285

未命名化合物

PRODUCTS

生成物

结构：CC(C)N1CCC(NC(=O)c2nc3cc(S(=O)(=O)CCO)ccc3n2CC(=O)Nc2ccc(Cl)cn2)CC1

HCID67011891

未命名化合物

结构：CC(C)N1CCC(NC(=O)c2nc3ccc(S(=O)(=O)CCO)cc3n2CC(=O)Nc2ccc(Cl)cn2)CC1

HCID67013322

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

1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide and 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-6-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide were prepared by a procedure according to example 29 starting from 1 g (2.5 mmol) crude 5-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide and 758.9 mg (3.04 mmol) 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide. 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-e3c9e4155de642c1a2392901f60027ef
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

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