Trifluoroacetic acid → HCID 18447431, compound

HRID 1269876Notes

Reaction equation

HRID 1269876 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][CH:18]([NH:23][C:24]1[C:25]([CH3:39])=[C:26]3[C:30](=[CH:31][CH:32]=1)[N:29](C1CCCCO1)[N:28]=[CH:27]3)[CH2:19]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH2:8]([N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][CH:18]([NH:23][C:24]1[C:25]([CH3:39])=[C:26]3[C:30](=[CH:31][CH:32]=1)[NH:29][N:28]=[CH:27]3)[CH2:19]2)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 516892Sodium BicarbonateHCID 18447432HCID 18447432, compound

Product 1

HCID 18447431HCID 18447431, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of the N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (273 mg, 0.634 mmol) obtained in Example 499 in dichloromethane (9 ml), and the resulting mixture was stirred at room temperature for 30 minutes. Then, trifluoroacetic acid (1 ml) was added thereto and stirred for another 30 minutes, and the resulting mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. 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, 6 plates, eluent: chloroform/methanol=6/1) to obtain N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-4-methyl-1H-indazol-5-amine (142 mg, 65%).

Workup

  1. stirringstirred for another 30 minutes
  2. extractionextracted with chloroform
  3. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by a preparative thin-layer chromatography (200×200×0.5 mm, 6 plates, eluent: chloroform/methanol=6/1)

Sources & evidence

ORD record
ord-2f28f007b0d94e589b01c816ee90db73
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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