Trifluoroacetic acid → N-(1H-indazol-5-yl)-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)methanesulfonamide

HRID 1269887Notes

Reaction equation

HRID 1269887 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:11]1[CH:16]2[CH2:17][CH2:18][CH:12]1[CH2:13][CH:14]([N:19]([C:24]1[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=1)[N:29](C1CCCCO1)[N:28]=[CH:27]3)[S:20]([CH3:23])(=[O:22])=[O:21])[CH2:15]2)[CH2:9][CH3:10].C(=O)([O-])O.[Na+]>ClCCl>[NH:29]1[C:30]2[C:26](=[CH:25][C:24]([N:19]([CH:14]3[CH2:15][CH:16]4[N:11]([CH2:8][CH2:9][CH3:10])[CH:12]([CH2:18][CH2:17]4)[CH2:13]3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:32][CH:31]=2)[CH:27]=[N:28]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18447449N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-N-(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-methanesulfonamide

Product 1

HCID 18447356N-(1H-indazol-5-yl)-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)methanesulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.2 ml) was added to a solution of N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-N-(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)-methanesulfonamide (19 mg, 0.0425 mmol) in dichloromethane (0.8 ml), and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a preparative thin-layer chromatography (200×200×0.5 mm, eluent: chloroform/methanol=9/1) to obtain N-(1H-indazol-5-yl)-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)methanesulfonamide (6 mg, 40%).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by a preparative thin-layer chromatography (200×200×0.5 mm, eluent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-24984b54e6ba4de19ef76c2becdfaece
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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