Acetic Anhydride → trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639853Notes

Reaction equation

HRID 1639853 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][NH2:15])=[N:3]1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][NH:15][C:23](=[O:25])[CH3:24])=[N:3]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59334500trans-1-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine

Product 1

HCID 59334573trans-N-{[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 52.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of trans-1-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine (100 mg, 0.497 mmol) and triethylamine (104 μL, 0.746 mmol) in tetrahydrofuran (5 mL) was added acetic anhydride (70.5 μL, 0.746 mmol) under ice-cooling, and the mixture was stirred at room temperature 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→10/90) and recrystallization (ethyl acetate/hexane) to give the title compound (63.2 mg, yield 52%).

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→10/90) and recrystallization (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2fdf6134d1934f00ba1c1152af33ab0f
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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