Sodium Hydroxide → HCID 22024528, compound

HRID 501013Notes

Reaction equation

HRID 501013 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([N:20]([CH2:28][CH2:29][CH3:30])C(=O)OC(C)(C)C)=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1.Cl.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([C:15]([NH:20][CH2:28][CH2:29][CH3:30])=[C:16]([CH2:18][CH3:19])[N:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 22024486tert-butyl N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-propylcarbamate

Product 1

HCID 22024528HCID 22024528, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl N-[8-(2,4-dichlorophenyl)-2-ethylimidazo[1,2-a]pyrazin-3-yl]-N-propylcarbamate was dissolved in ethyl acetate (1 mL), then a 4N hydrochloric acid-ethyl acetate solution (1.9 mL, 7.4 mmol) 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 thereto, which was extracted with ethyl acetate. The organic layers were combined, which was dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:4) to give the title compound (151 mg) as a yellow oil.

Workup

  1. temperatureUnder ice-cooling
  2. extractionwhich was extracted with ethyl acetate
  3. dry with materialwhich was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:4)

Sources & evidence

ORD record
ord-4ff884c7e51a4a2ebad3250cf40e1b76
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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