Triethylamine → trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}cyclopropanecarboxamide

HRID 1639875Notes

Reaction equation

HRID 1639875 reaction equation
[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH2:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:1][C:2]1[CH:15]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH:14][C:26]([CH:23]3[CH2:25][CH2:24]3)=[O:27])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 59334541trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine

Product 1

HCID 59334617trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}cyclopropanecarboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of trans-1-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine (100 mg, 0.497 mmol) and triethylamine (83.2 μL, 0.596 mmol) in tetrahydrofuran (5 mL) was added cyclopropanecarbonyl chloride (49.6 μL, 0.547 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 10 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=35/65→90/10) to give the title compound (87.0 mg, yield 65%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 10 min
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=35/65→90/10)

Sources & evidence

ORD record
ord-46fec7153f0d4a71a792e162382c9303
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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