Sodium Iodide → HCID 68550400, compound

HRID 731716Notes

Reaction equation

HRID 731716 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].C([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)(OC(C)(C)C)=O.[Na+].[I-]>CO>[ClH:1].[CH:14]([C:6]1[C:5]([C:3](=[O:4])[CH:2]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]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 143452tert-Butyl piperazine-1-carboxylateHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 68550400HCID 68550400, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 980 mg (3.90 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, 1.45 g (4 mmol) of N-Boc-piperazine and 100 mg of NaI in 10 ml of MeOH was stirred at 50-70° C. for 5 hours. 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 150 mg of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-(piperazin-1-yl)propan-1-one hydrochloride. Compound 1037.

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-f6330fabecd14853b8eafcfc1d8329c0
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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