Sodium Hydroxide → N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine

HRID 500999Notes

Reaction equation

HRID 500999 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:9]([N:14]([CH2:22][CH2:23][CH3:24])C(=O)OC(C)(C)C)=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[N:4]([C:9]([NH:14][CH2:22][CH2:23][CH3:24])=[C:10]([S:12][CH3:13])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 22024676tert-Butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylcarbamate

Product 1

HCID 22024391N-[8-Bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl N-[8-bromo-6-methyl-2-(methylsulfanyl)imidazo[1,2-a]pyridin-3-yl]-N-propylcarbamate was dissolved in ethyl acetate (5 mL), then a 4N hydrochloric acid-ethyl acetate solution (10 mL) was added thereto at room temperature, and the mixture was stirred at room temperature for 20 hours. Under ice-cooling, a 5N aqueous sodium hydroxide solution was added to neutralize the solution, which was extracted with ethyl acetate. The organic layers were combined, which was dried over anhydrous magnesium sulfate, and evaporated, to give the title compound (103 mg) as a yellow amorphous.

Workup

  1. temperatureUnder ice-cooling
  2. extractionwas extracted with ethyl acetate
  3. dry with materialwhich was dried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5c3cab7c33bc4e70a415474ec0516ba5
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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