Trifluoroacetic acid → HCID 57860479, compound

HRID 1947124Notes

Reaction equation

HRID 1947124 reaction equation
[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1)=[O:28].FC(F)(F)C(O)=O>>[CH3:1][O:2][C:3]1[C:7]2[C:8](=[O:25])[N:9]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]=2[N:5]([CH3:26])[C:4]=1[C:27]([NH:29][CH:30]1[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]1)=[O:28]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66893129HCID 66893129, compound

Product 1

HCID 57860479HCID 57860479, compoundYield 85.4%

Procedure

The thus-obtained tert-butyl 4-({[3-methoxy-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl]carbonyl}amino)piperidine-1-carboxylate (610 mg) and trifluoroacetic acid (5 mL) were stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, saturated sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=20/1), and the obtained solid was recrystallized from ethyl acetate-ethanol to give the title compound (430 mg, 85%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated sodium hydrogen carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate/methanol=20/1)
  8. customthe obtained solid was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-11b712f074d740568ff9dbd0a9743190
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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