Sodium Iodide → 1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(4-methylpiperazin-1-yl)propan-1-one hydrochloride

HRID 731714Notes

Reaction equation

HRID 731714 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].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[Na+].[I-]>CO>[ClH:1].[CH:14]([C:6]1[C:5]([C:3](=[O:4])[CH:2]([N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]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 531671-MethylpiperazineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 685463291-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(4-methylpiperazin-1-yl)propan-1-one hydrochlorideYield 21.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 500 mg (2 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, 272 μl (2.4 mmol) of N-methylpiperazine and 50 mg of NaI in 4 ml of MeOH was stirred at RT for 4 days. The solvent was removed and the crude residue 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 150 mg of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(4-methylpiperazin-1-yl)propan-1-one hydrochloride (shown in neutral form above). Compound 1035.

Workup

  1. customThe solvent was removed
  2. customthe crude residue was purified on an Al2O3 column
  3. additionThe fractions containing
  4. custompurified product
  5. customto obtain a precipitate
  6. customRecrystallization from isopropanol/ether

Sources & evidence

ORD record
ord-019d37ea9773456cb3152d3c02f66502
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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