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

HRID 887812Notes

Reaction equation

HRID 887812 reaction equation
Cl.[CH3:2][C:3]1[CH:17]=[C:6]2[C:7]3[CH:13]([CH2:14][CH2:15][NH2:16])[CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:2][C:3]1[CH:17]=[C:6]2[C:7]3[CH:13]([CH2:14][CH2:15][NH:16][C:25](=[O:27])[CH3:26])[CH2:12][CH2:11][C:8]=3[CH:9]=[CH:10][N:5]2[N:4]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 687018192-(2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine hydrochloride

Product 1

HCID 59145922N-[2-(2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamideYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 2-(2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine hydrochloride obtained in Reference Example 43 and triethylamine (1.36 mL, 9.76 mmol) in tetrahydrofuran (5 mL) was added acetic anhydride (115 μL, 1.22 mmol) under ice-cooling, and the mixture was stirred for 15 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) and recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (56.6 mg, total yield from Reference Example 43, 45%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) and recrystallization (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-7fd67a661cce4f4887ea1de942f2400c
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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