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

HRID 1639864Notes

Reaction equation

HRID 1639864 reaction equation
Cl.Cl.[F:3][C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH3:13])[N:9]=2)[C:5]=1[C@@H:14]1[CH2:16][C@H:15]1[CH2:17][NH2:18].C(N(CC)CC)C.[C:26](OC(=O)C)(=[O:28])[CH3:27]>O1CCCC1.C(=O)([O-])O.[Na+]>[F:3][C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH3:13])[N:9]=2)[C:5]=1[C@@H:14]1[CH2:16][C@H:15]1[CH2:17][NH:18][C:26](=[O:28])[CH3:27]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 667206571-[(1R,2R)-2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride

Product 1

HCID 59334591trans-N-{[2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-[(1R,2R)-2-(5-fluoro-2-methyl-2H-indazol-4-yl) cyclopropyl]methanamine dihydrochloride (258 mg, 0.883 mmol) and triethylamine (615 μL, 4.415 mmol) in tetrahydrofuran (9 mL) was stirred at room temperature for 20 min. To the reaction solution was added acetic anhydride (125 μL, 1.325 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 15 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 (227 mg, yield 98%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 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-56e7b9d819904719abb089873bc8b7a2
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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