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

HRID 2389944Notes

Reaction equation

HRID 2389944 reaction equation
[CH2:1]([C:3]1[C:14]([CH:15]([CH3:18])[CH2:16][NH2:17])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].C(N(CC)CC)C.[C:26](Cl)(=[O:28])[CH3:27].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([C:3]1[C:14]([CH:15]([CH3:18])[CH2:16][NH:17][C:26](=[O:28])[CH3:27])=[C:6]2[C:7]3[CH2:13][CH2:12][O:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 591793732-(2-Ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propan-1-amine

Product 1

HCID 24955344N-[2-(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propyl]acetamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-ethyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)propan-1-amine (118 mg, 0.481 mmol) and triethylamine (134 μL, 0.961 mmol) in tetrahydrofuran (5 mL) was added acetyl chloride (90.9 μL, 0.962 mmol) under ice-cooling, and the mixture was stirred at room temperature for 10 min. A saturated aqueous sodium hydrogen carbonate solution (100 μL) was added and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (133 mg, yield 96%).

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-2d59d0b9bb9741818ebf0dc10e32dee3
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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