3-Hydroxyazetidine → 1-[2-(4-Chloro-phenyl)-ethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 18566Notes

Reaction equation

HRID 18566 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([OH:21])=O)[C:13]=3[N:12]=[C:11]2[C:22](=[O:33])[NH:23][CH:24]2[CH2:29][CH2:28][N:27]([CH:30]([CH3:32])[CH3:31])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.[OH:34][CH:35]1[CH2:38][NH:37][CH2:36]1>>[CH:30]([N:27]1[CH2:28][CH2:29][CH:24]([NH:23][C:22]([C:11]2[N:10]([CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([N:37]4[CH2:38][CH:35]([OH:34])[CH2:36]4)=[O:21])[C:13]=3[N:12]=2)=[O:33])[CH2:25][CH2:26]1)([CH3:31])[CH3:32]

Participants

3

Reactant 2

HCID 15142903-HydroxyazetidineHCID 670123531-[2-(4-Chloro-phenyl)-ethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 670119391-[2-(4-Chloro-phenyl)-ethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Procedure

1-[2-(4-Chloro-phenyl)-ethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure according to example 22 starting from 150 mg (0.29 mmol) 1-[2-(4-Chloro-phenyl)-ethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid and 23.4 mg (0.32 mmol) 3-hydroxy-azetidine. The title compound was obtained as its formiate in form a white amorphous solid.

Workup

  1. custom1-[2-(4-Chloro-phenyl)-ethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure

Sources & evidence

ORD record
ord-b7a3483c68dd4a4d851dbaf158682c74
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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