Trifluoroacetic acid → HCID 25117679, compound

HRID 547261Notes

Reaction equation

HRID 547261 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:15][CH2:14][C@@H:13]([NH:16]C(=O)OC(C)(C)C)[CH2:12]3)=[CH:8][CH:9]=2)[C:4]([S:24]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[N:3]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]3[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]3)=[CH:8][CH:9]=2)[C:4]([S:24]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[N:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86624979HCID 86624979, compound

Product 1

HCID 25117679HCID 25117679, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {(3R)-1-[1-methyl-3-(naphthalen-1-ylsulfonyl)-1H-indazol-5-yl]pyrrolidin-3-yl}carbamate (0.200 g, 0.395 mmol) was dissolved in dichloromethane and to this was added trifluoroacetic acid (1 mL). The reaction mixture was stirred at room temperature over night. The solvent and excess trifluoroacetic acid was evaporated and the residue was dissolved in ethyl acetate. The organic mixture was washed with saturated aqueous potassium carbonate. The solvent was evaporated to afford a pure (3R)-1-[1-methyl-3-(naphthalen-1-ylsulfonyl)-1H-indazol-5-yl]pyrrolidin-3-amine (15, 0.147 g, 92%).

Workup

  1. customThe solvent and excess trifluoroacetic acid was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic mixture was washed with saturated aqueous potassium carbonate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9af7514936d34c48adc42578f522387f
Source dataset
uspto-grants-2011_05
Patent number
US07939520B2

Reaction notes

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