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

HRID 887807Notes

Reaction equation

HRID 887807 reaction equation
Cl.[CH:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]3[CH2:11][CH2:12][CH:13]([CH2:14][CH2:15][NH2:16])[C:7]=3[C:6]=12.C(N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25].O>O1CCCC1>[CH:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]3[CH2:11][CH2:12][CH:13]([CH2:14][CH2:15][NH:16][C:24](=[O:26])[CH3:25])[C:7]=3[C:6]=12

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 686989162-(8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine hydrochloride

Product 1

HCID 59145927N-[2-(8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamideYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine hydrochloride (45.5 mg, 0.191 mmol) and triethylamine (206 μL, 1.48 mmol) in tetrahydrofuran (1.5 mL) was added acetic anhydride (42.0 μL, 0.444 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 min. Water (50 μL) was added, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (22.4 mg, yield 48%).

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→10/90) and recrystallization (ethyl acetate/diisopropyl ether)

Sources & evidence

ORD record
ord-bb5ddf7c58a2488f8c57391c8168d80f
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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