Acetic Anhydride → N-{[(1S,2S)-2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide

HRID 1639863Notes

Reaction equation

HRID 1639863 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 667206561-[(1S,2S)-2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride

Product 1

HCID 59334630N-{[(1S,2S)-2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamideYield 103.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 1-[(1S,2S)-2-(5-fluoro-2-methyl-2H-indazol-4-yl)cyclopropyl]methanamine dihydrochloride (230 mg, 0.787 mmol) and triethylamine (549 μL, 3.936 mmol) in tetrahydrofuran (8 mL) was stirred at room temperature for 20 min. To the reaction solution was added acetic anhydride (112 μL, 1.181 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 (213 mg, yield 99%).

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-9b33cf03487d44199b81bdfb436202ff
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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