Acetic Anhydride → N-[2-(8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethyl]acetamide

HRID 2389933Notes

Reaction equation

HRID 2389933 reaction equation
[C:1]1([CH2:13][CH2:14][NH2:15])[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]3[O:10][CH2:11][CH2:12][C:6]=3[C:5]=12.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]1([CH2:13][CH2:14][NH:15][C:23](=[O:25])[CH3:24])[CH:2]=[N:3][N:4]2[CH:9]=[CH:8][C:7]3[O:10][CH2:11][CH2:12][C:6]=3[C:5]=12

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 591794222-(8,9-Dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine

Product 1

HCID 24812809N-[2-(8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethyl]acetamideYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine (75.0 mg, 0.369 mmol) and triethylamine (105 μL, 0.753 mmol) in tetrahydrofuran (4 mL) was added acetic anhydride (70.0 μL, 0.741 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. A saturated aqueous sodium hydrogen carbonate solution (50 μL) was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) and recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (42.1 mg, yield 47%).

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→5/95) and recrystallization (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-c1a0bf7508e3496cba9411fcda610307
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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