Acetic Anhydride → trans-N-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639862Notes

Reaction equation

HRID 1639862 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15][NH2:16].C(N(CC)CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25]>O1CCCC1.C(=O)([O-])O.[Na+]>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[C@@H:12]1[CH2:14][C@H:13]1[CH2:15][NH:16][C:24](=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59334529trans-1-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine

Product 1

HCID 59334591trans-N-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of trans-1-[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine (95.0 mg, 0.433 mmol) and triethylamine (72.4 μL, 0.520 mmol) in tetrahydrofuran (5 mL) was added acetic anhydride (45.1 μL, 0.477 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 (NH, methanol/ethyl acetate=0/100→5/95) to give the title compound (97 mg, yield 86%).

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 (NH, methanol/ethyl acetate=0/100→5/95)

Sources & evidence

ORD record
ord-d515d0a97bd449258871d6b7a3a9e6d1
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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