Imidazole → HCID 22387842, compound

HRID 1072920Notes

Reaction equation

HRID 1072920 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([CH2:23]OS(C)(=O)=O)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].[NH:29]1[CH:33]=[CH:32][N:31]=[CH:30]1.O>ClCCl>[Cl:1][C:2]1[CH:22]=[C:21]([CH2:23][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 22387738HCID 22387738, compound

Product 1

HCID 22387842HCID 22387842, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(2-chloro-4-((methanesulfonyloxy)methyl)benzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (300 mg) in dichloromethane (6.0 ml) was added imidazole (193 mg), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was washed with diethyl ether, and collected by filtration to give the objective compound (213 mg) as a pale-yellow powder.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. washThe residue was washed with diethyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-00a20056089d484b9e85e61c8be03f86
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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