N-Methylbenzylamine → 2-(Benzyl(methyl)amino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one

HRID 731718Notes

Reaction equation

HRID 731718 reaction equation
Cl[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][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO.[Na+].[I-]>[CH2:20]([N:19]([CH3:18])[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:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 7669N-MethylbenzylamineHCID 215857512-Chloro-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone

Product 1

HCID 578375142-(Benzyl(methyl)amino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-oneYield 33.4%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.37 g (13.4 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one, 1.74 ml (13.4 mmol) of N-methyl benzylamine and 50 mg of NaI in 15 ml of MeOH was refluxed overnight. The mixture obtained after evaporation of the solvent was purified on an Al2O3 column, and recrystallized from ether/hexane to obtain 1.5 g of 2-(benzyl(methyl)amino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one. Compound 1041.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture obtained
  3. customafter evaporation of the solvent
  4. customwas purified on an Al2O3 column
  5. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-5fc9445f210a4892afe0d8271376d6b7
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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