Sodium Iodide → 1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochloride

HRID 731715Notes

Reaction equation

HRID 731715 reaction equation
[Cl:1][CH:2]([CH3:17])[C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=[O:4].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Na+].[I-]>CO>[ClH:1].[CH:14]([C:6]1[C:5]([C:3](=[O:4])[CH:2]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])=[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]2[N:7]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8082PiperidineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 685469031-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochlorideYield 26.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 500 mg (2 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, 478 ul (4.8 mmol) of piperidine and 50 mg of NaI in 4 ml of MeOH was stirred at 50° C. overnight. The residue obtained after evaporation of the solvent was purified on an Al2O3 column. The fractions containing purified product were titrated with 4N HCl-dioxane to obtain a precipitate. Recrystallization from isopropanol/ether produced 175 mg of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperidin-1-yl)propan-1-one hydrochloride. Compound 1036.

Workup

  1. customThe residue obtained
  2. customafter evaporation of the solvent
  3. customwas purified on an Al2O3 column
  4. additionThe fractions containing
  5. custompurified product
  6. customto obtain a precipitate
  7. customRecrystallization from isopropanol/ether

Sources & evidence

ORD record
ord-c0635d6c67444cab97a1d7d776cda9ca
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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