Trifluoroacetic acid → HCID 137010788, compound

HRID 2206259Notes

Reaction equation

HRID 2206259 reaction equation
[F:1][C:2]1[C:3]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([O:19][CH3:20])[C:13]=3[C:12]([C:21]3[CH:22]=[N:23][N:24](COCC[Si](C)(C)C)[CH:25]=3)=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:1][C:2]1[C:3]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([O:19][CH3:20])[C:13]=3[C:12]([C:21]3[CH:25]=[N:24][NH:23][CH:22]=3)=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 131735845HCID 131735845, compound

Product 1

HCID 137010788HCID 137010788, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-2-(4-methoxy-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)benzonitrile (400 mg) in dichloromethane (4 mL) was added trifluoroacetic acid (1 mL), and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added aqueous sodium carbonate solution. The organic layer was separated, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (115 mg).

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-0fc3a3fb232e421ca3e1e938dac45cf8
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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