Acetic Anhydride → trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}acetamide

HRID 1639854Notes

Reaction equation

HRID 1639854 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH2:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH:14][C:23](=[O:25])[CH3:24])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59334541trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine

Product 1

HCID 59334538trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}acetamideYield 54.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of trans-1-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine (200 mg, 0.994 mmol) and triethylamine (208 μL, 1.49 mmol) in tetrahydrofuran (10 mL) was added acetic anhydride (113 μL, 1.20 mmol) under ice-cooling, and the mixture was stirred at room temperature for 5 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/hexane) to give the title compound (131 mg, yield 54%).

Workup

  1. temperaturecooling
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eda1003cb37142ba896e20e85576a16e
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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