2-Bromo-N-(5-chloro-2-pyridinyl)acetamide → 4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 18604Notes

Reaction equation

HRID 18604 reaction equation
[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][CH:20]=[C:21]([O:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:15]=3[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Br[CH2:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=1)=[O:36]>>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[N:17]([CH2:34][C:35](=[O:36])[NH:37][C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][N:39]=3)[C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([O:22][CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:27])[CH3:28])[C:15]=3[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 865958844-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Product 1

HCID 865958834-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Procedure

4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure according to example 108 (v) starting from 670.0 mg (1.45 mmol) 4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide and 362.8 mg (1.45 mmol) 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide. Final purification by flash-chromatography on silica gel using ethyl acetate as eluent gave the title compound as a brown oil.

Workup

  1. custom4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide was prepared by a procedure
  2. customFinal purification by flash-chromatography on silica gel

Sources & evidence

ORD record
ord-1403a15b49594ce78826d83dc4628418
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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