Trifluoroacetic acid → HCID 18447355, compound

HRID 1269888Notes

Reaction equation

HRID 1269888 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:23]1[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=1)[N:28](C1CCCCO1)[N:27]=[CH:26]3)[C:20](=[O:22])[CH3:21])[CH2:15]2)[CH2:9][CH3:10].C(=O)([O-])O.[Na+]>ClCCl>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([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)[C:20](=[O:22])[CH3:21])=[CH:31][CH:30]=2)[CH:26]=[N:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18447448HCID 18447448, compound

Product 1

HCID 18447355HCID 18447355, compoundYield 64,643.602%

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)-acetamide (35 mg, 0.0853 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. 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, whereby N-(1H-indazol-5-yl)-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)acetamide (18 g, 64%) was obtained.

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

Sources & evidence

ORD record
ord-a7f9afc8188e487abc13d815191e06b0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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