Trifluoroacetic acid → HCID 24752944, compound

HRID 561117Notes

Reaction equation

HRID 561117 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([S:26]CC4C=CC(OC)=CC=4)[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[C:12]=3[F:14])[C:7](=[O:36])[C:6]([C:37]([OH:39])=[O:38])=[CH:5]2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([SH:26])[C:10]([F:25])=[C:11]([NH:15][CH2:16][CH2:17][NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)[C:12]=3[F:14])[C:7](=[O:36])[C:6]([C:37]([OH:39])=[O:38])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59002944HCID 59002944, compound

Product 1

HCID 24752944HCID 24752944, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A mixture of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-(4-methoxybenzylthio)-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (290 mg, 0.525 mmol) and trifluoroacetic acid (1.5 mL) in anisole (1.5 mL) was stirred at room temperature for 24 h. The mixture was concentrated in vacuo. The residue was dissolved in water (5 mL), then added saturated aq. NaHCO3 until pH=7. The resulting precipitate was combined by filtration. Recrystallization of the cake from MeOH (30 mL) gave 1-cyclopropyl-6,8-difluoro-1,4-dihydro-5-mercapto-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid as a pale yellow solid (155 mg, 68%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. filtrationThe resulting precipitate was combined by filtration
  4. customRecrystallization of the cake from MeOH (30 mL)

Sources & evidence

ORD record
ord-f5b86946d2934aa2b60cbb09fea65355
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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