Water → ethyl 9-[2-(acetylamino)ethyl]-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 887808Notes

Reaction equation

HRID 887808 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH3:21])[C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:29](OC(=O)C)(=[O:31])[CH3:30].O>O1CCCC1>[C:29]([NH:1][CH2:2][CH2:3][CH:4]1[C:8]2[C:9]3[N:10]([N:13]=[C:14]([CH3:21])[C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5]1)(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59145868ethyl 9-(2-aminoethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

Product 1

HCID 59145881ethyl 9-[2-(acetylamino)ethyl]-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 9-(2-aminoethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (50.0 mg, 0.174 mmol) and triethylamine (36.4 μL, 0.261 mmol) in tetrahydrofuran (2 mL) was added acetic anhydride (24.7 μL) under ice-cooling, and the mixture was stirred at room temperature for 30 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) and recrystallization (diisopropyl ether) to give the title compound (32.1 mg, yield 56%).

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→5/95) and recrystallization (diisopropyl ether)

Sources & evidence

ORD record
ord-3490e6d5af324b348bdf183204ee013c
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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