Acetic Anhydride → N-[2-(2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamide

HRID 887826Notes

Reaction equation

HRID 887826 reaction equation
[C:1]1([C:7]2[CH:21]=[C:10]3[C:11]4[CH:17]([CH2:18][CH2:19][NH2:20])[CH2:16][CH2:15][C:12]=4[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30].C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]1([C:7]2[CH:21]=[C:10]3[C:11]4[CH:17]([CH2:18][CH2:19][NH:20][C:29](=[O:31])[CH3:30])[CH2:16][CH2:15][C:12]=4[CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 591458772-(2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine

Product 1

HCID 25025105N-[2-(2-phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamideYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Phenyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine (200 mg, 0.721 mmol) was dissolved in tetrahydrofuran (7 mL), triethylamine (201 μL, 1.44 mmol) and acetic anhydride (81.8 μL, 0.865 mmol) were added under ice-cooling, and the mixture was stirred for 15 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (195 mg, total yield from Reference Example 65, 69%).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9ffd79b7994e4cfb971d479b54ea6e6c
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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