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

HRID 887825Notes

Reaction equation

HRID 887825 reaction equation
[CH3:1][C:2]1[CH:16]=[C:5]2[C:6]3[CH:12]([CH2:13][CH2:14][NH2:15])[CH2:11][CH2:10][C:7]=3[CH:8]=[CH:9][N:4]2[N:3]=1.C(N(CC)CC)C.[CH:24]1([C:27](Cl)=[O:28])[CH2:26][CH2:25]1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1[CH:16]=[C:5]2[C:6]3[CH:12]([CH2:13][CH2:14][NH:15][C:27]([CH:24]4[CH2:26][CH2:25]4)=[O:28])[CH2:11][CH2:10][C:7]=3[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 591458402-(2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethanamine

Product 1

HCID 25025106N-[2-(2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]cyclopropanecarboxamideYield 74.1%

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 (69.7 mg, 0.324 mmol) and triethylamine (90.3 μL, 0.648 mmol) in tetrahydrofuran (3 mL) was added cyclopropanecarbonyl chloride (35.3 μL, 0.389 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 solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (68.0 mg, yield 74%).

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-5fbe11360dde4e80a8fddde87d458ed7
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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