Trifluoroacetic acid → 1-Methyl-6-[3-(piperidin-4-yl-pyridin-4-ylmethyl-amino)-propoxy]-1H-quinolin-2-one

HRID 69036Notes

Reaction equation

HRID 69036 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]([CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:34]=[C:35]3[C:40](=[CH:41][CH:42]=2)[N:39]([CH3:43])[C:38](=[O:44])[CH:37]=[CH:36]3)[CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:43][N:39]1[C:40]2[C:35](=[CH:34][C:33]([O:32][CH2:31][CH2:30][CH2:29][N:21]([CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[CH2:22][C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)=[CH:42][CH:41]=2)[CH:36]=[CH:37][C:38]1=[O:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669618574-{[3-(1-Methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 669607031-Methyl-6-[3-(piperidin-4-yl-pyridin-4-ylmethyl-amino)-propoxy]-1H-quinolin-2-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (30 ml) was added to a dichloromethane solution (10 ml) of 4-{[3-(1-methyl-2-oxo-1,2-dihydro-quinolin-6-yloxy)-propyl]-pyridin-4-ylmethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester (1.08 g), and the mixture was stirred at room temperature overnight. The reaction mixture was condensed under reduced pressure. PL-HCO3 (40 g) was added to the dichloromethane solution of the residue and followed by celite filtration. The filtrate was condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=4:1). The purified product was condensed under reduced pressure to give the title compound (758 mg) as an orange oil.

Workup

  1. customcondensed under reduced pressure
  2. filtrationfollowed by celite filtration
  3. customcondensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=4:1)
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-5b147059042d4e95823854064fe10ee3
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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