3-Hydroxyazetidine → 4-(3-Hydroxy-azetidine-1-carbonyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 18565Notes

Reaction equation

HRID 18565 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[C:16]3[CH:27]=[CH:28][CH:29]=[C:30]([C:31](O)=[O:32])[C:15]=3[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[OH:34][CH:35]1[CH2:38][NH:37][CH2:36]1>>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)[C:16]3[CH:27]=[CH:28][CH:29]=[C:30]([C:31]([N:37]4[CH2:38][CH:35]([OH:34])[CH2:36]4)=[O:32])[C:15]=3[N:14]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 15142903-HydroxyazetidineHCID 670118282-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 670123934-(3-Hydroxy-azetidine-1-carbonyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Procedure

4-(3-Hydroxy-azetidine-1-carbonyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure according to example 22 starting from 150 mg (0.287 mmol) 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-4-carboxylic acid and 23.0 mg (0.315 mmol) 3-hydroxy-azetidine. The title compound was obtained as its formiate in form a white amorphous solid.

Workup

  1. custom4-(3-Hydroxy-azetidine-1-carbonyl)-1-(3-methoxy-benzyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure

Sources & evidence

ORD record
ord-b0de4ad7d01f41229ee259b5f7cd3fe3
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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