Sodium Hydroxide → N-(7-Bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylamine

HRID 2253364Notes

Reaction equation

HRID 2253364 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:23][CH3:24])[C:10]([N:11]([CH2:19][CH:20]3[CH2:22][CH2:21]3)C(=O)OC(C)(C)C)=[C:6]2[CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:23][CH3:24])[C:10]([NH:11][CH2:19][CH:20]3[CH2:21][CH2:22]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21084186tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 58801654N-(7-Bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude tert-butyl N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylcarbamate dissolved in ethyl acetate (10 mL) was added 4N hydrochloric acid/ethyl acetate (30 mL), and the reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, a 5N aqueous sodium hydroxide solution was added to the reaction mixture while cooling with ice for neutralization. The reaction mixture was extracted with ethyl acetate, and after washing the organic extract with water and brine, it was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (20 g) and the title compound (479 mg) was obtained as a yellow oil from the ethyl acetate:n-hexane (1:3) fraction.

Workup

  1. customAfter completion of the reaction
  2. temperaturewhile cooling with ice for neutralization
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washafter washing the
  5. extractionorganic extract with water and brine, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (20 g)

Sources & evidence

ORD record
ord-6311f97382234d868b182b76473884ca
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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