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

HRID 887815Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH2:21][CH3:22])[C:15]=3C(OCC)=O)[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31].O>Cl.O1CCCC1>[CH2:21]([C:14]1[CH:15]=[C:9]2[C:8]3[CH:4]([CH2:3][CH2:2][NH:1][C:30](=[O:32])[CH3:31])[CH2:5][CH2:6][C:7]=3[CH:12]=[CH:11][N:10]2[N:13]=1)[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 9-(2-aminoethyl)-2-ethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (81.0 mg, 0.269 mmol) in 12M hydrochloric acid (3 mL) was stirred at 100° C. for 3 days, and the mixture was concentrated under reduced pressure. To a mixture of the residue and triethylamine (375 μL, 2.69 mmol) in tetrahydrofuran (2.7 mL) was added acetic anhydride (76.3 μL, 0.807 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→5/95) to give the title compound (62.9 mg, yield 85%).

Workup

concentrationthe mixture was concentrated under reduced pressure
temperaturecooling
stirringthe mixture was stirred at room temperature for 15 min
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record: ord-1aececc5591e4f4fb0411629c842401d
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247429B2

Reaction notes

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