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

HRID 1639878Notes

Reaction equation

HRID 1639878 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.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 59334541trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine

Product 1

HCID 66720594trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}benzamideYield 67.3%

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 (50.0 mg, 0.248 mmol) and triethylamine (41.6 μL, 0.298 mmol) in tetrahydrofuran (2.5 mL) was added benzoyl chloride (31.7 μL, 0.273 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 5 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 (methanol/ethyl acetate=0/100→5/95) 15 and silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95) to give the title compound (51.0 mg, yield 67%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 5 min
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) 15 and silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-674effc8dd26402ab8aff64b5dfe2cf7
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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