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

HRID 2389945Notes

Reaction equation

HRID 2389945 reaction equation
[CH2:1]([C:3]1[C:15]([CH2:16][CH2:17][NH2:18])=[C:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[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:15]([CH2:16][CH2:17][NH:18][C:26](=[O:28])[CH3:27])=[C:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[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 591793642-(2-Ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine

Product 1

HCID 59179440N-[2-(2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethyl]acetamideYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-ethyl-8-methylfuro[3,2-c]pyrazolo[1,5-a]pyridin-1-yl)ethanamine (100 mg, 0.411 mmol) and triethylamine (85.9 μL, 0.616 mmol) in tetrahydrofuran (4 mL) was added acetyl chloride (58.3 μL, 0.617 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) and recrystallization (ethyl acetate/hexane) to give the title compound (59.7 mg, yield 51%).

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) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0cad48246e58460588fed9a583b824ec
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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