3-Hydroxyazetidine → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 18617Notes

Reaction equation

HRID 18617 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][C:20]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[C:21]([C:22](O)=[O:23])[C:16]=4[N:15]=[C:14]3[C:31](=[O:42])[NH:32][CH:33]3[CH2:38][CH2:37][N:36]([CH:39]([CH3:41])[CH3:40])[CH2:35][CH2:34]3)[CH:8]=2)=[CH:4][CH:3]=1.[NH:43]1[CH2:46][CH:45]([OH:47])[CH2:44]1>>[CH:39]([N:36]1[CH2:37][CH2:38][CH:33]([NH:32][C:31]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[C:17]3[CH:18]=[CH:19][C:20]([O:25][CH2:26][C:27]([F:30])([F:28])[F:29])=[C:21]([C:22]([N:43]4[CH2:46][CH:45]([OH:47])[CH2:44]4)=[O:23])[C:16]=3[N:15]=2)=[O:42])[CH2:34][CH2:35]1)([CH3:41])[CH3:40]

Participants

3

Reactant 2

HCID 15142903-HydroxyazetidineHCID 670113761-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-4-carboxylic acid

Product 1

HCID 670125121-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Procedure

1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure according to example 22 starting from 50.0 mg (0.08 mmol) 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-4-carboxylic acid and 8.7 mg (0.12 mmol) azetidin-3-ol. The title compound was obtained as its formiate in form of a white amorphous solid.

Workup

  1. custom1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(3-hydroxy-azetidine-1-carbonyl)-5-(2,2,2-trifluoro-ethoxy)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure

Sources & evidence

ORD record
ord-752b5a6f722349418f257de0e8dce2bb
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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