Trifluoroacetic acid → HCID 135599923, compound

HRID 1175820Notes

Reaction equation

HRID 1175820 reaction equation
COC1C=CC(C[N:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3=[N:18][N:19]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:27][CH:26]=4)[C:20]([NH:21]C(=O)C)=[C:10]3[C:9]2=[O:39])=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>>[NH2:21][C:20]1[N:19]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:27][CH:26]=2)[N:18]=[C:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[NH:8][C:9](=[O:39])[C:10]=12

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 23153909HCID 23153909, compound

Product 1

HCID 135599923HCID 135599923, compoundYield 43.6%

Procedure

A mixture of N-{5-(4-methoxybenzyl)-4-oxo-2-[4-(2-piperidin-1-ylethyl)phenyl]-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-3-yl}acetamide (0.13 g), trifluoroacetic acid (2.5 ml), anisole (1 ml) and trifluoromethanesulfonic acid (0.5 ml) was stirred at room temperature for 26 hours. Ice and 2N aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with propylaminated silica gel column chromatography, and the obtained crystals were recrystallized from ethyl acetate to obtain the target compound (0.04 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified with propylaminated silica gel column chromatography
  6. customthe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eb1639c32a65448cb2e743c50326414d
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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