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

HRID 731713Notes

Reaction equation

HRID 731713 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][O: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][O: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 8083MorpholineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 685489951-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-morpholinopropan-1-one hydrochlorideYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 500 mg (2 mmol) 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one in 4 ml of MeOH was added 227 mg (2.6 mmol) of morpholine and 150 mg NaI. The mixture was stirred at RT for 3 days. The solvent was removed and the residue dissolved in 5 ml of ether, followed by titration with 4N HCl-dioxane to obtain a precipitate. Recrystallization from isopropanol/ether produced 200 mg of pure 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-morpholinopropan-1-one hydrochloride. Compound 1034.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in 5 ml of ether
  3. customto obtain a precipitate
  4. customRecrystallization from isopropanol/ether

Sources & evidence

ORD record
ord-4116f09804e846d180abc87bb2cc7ede
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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