Trifluoroacetic acid → HCID 23442300, compound

HRID 2119664Notes

Reaction equation

HRID 2119664 reaction equation
[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:5]=2[CH:4]=[N:3]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][N:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:5]=2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23442453HCID 23442453, compound

Product 1

HCID 23442300HCID 23442300, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of tert-butyl 4-(1,7-dimethyl-9-oxo-1,9-dihydro-4H-pyrazolo[4,3-b]quinolin-4-yl)-1-piperidinecarboxylate (EXAMPLE 64, step 1, 62 mg, 0.16 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (0.03 ml, 0.39 mmol) and the mixture was stirred at room temperature for 7 h and at 45° C. for 21 h. After evaporation, the residue was dissolved in dichloromethane (20 ml), washed with saturated aqueous sodium bicarbonate (20 ml) and dried over sodium sulfate. Removal of solvent gave 22 mg (47%) of the title compound as a white solid.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  4. dry with materialdried over sodium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-dfe25be50c6a4fa2b6e8019bbbf1e8df
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

Loading…