Réaction #46846

Équation de réaction

2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

CH3CN H2O

1-bromomethyl-3-methoxy-benzene

→

2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-3-(3-methoxy-benyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Solvants

formic acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONa 1:1 mixture of both isomers
2. 2
   AutreThese isomers could be separated by NP-HPLC
3. 3
   workup.ADDITIONa mixture of heptane, ethanol, methanol and diethyl amine as solvent

Mode opératoire

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.

Source