Potassium Hydroxide → 3-(1,4'-Bipiperidin-1'-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245157Notes

Reaction equation

HRID 245157 reaction equation
[OH-].[K+].[N:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[C:17]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[CH:35]=4)=[N:18][C:19]4[C:24]([C:25]=3[C:26]([O:28]C)=[O:27])=[CH:23][C:22]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:21][CH:20]=4)[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[N:3]1([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[C:17]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:41])([F:42])[F:43])[CH:35]=4)=[N:18][C:19]4[C:24]([C:25]=3[C:26]([OH:28])=[O:27])=[CH:23][C:22]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:21][CH:20]=4)[CH2:13][CH2:14]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71183054Methyl 3-(1,4'-bipiperidin-1'-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 674183633-(1,4'-Bipiperidin-1'-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 48.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (0.699 g, 12.46 mmol) in water (10 mL) was added to a solution of methyl 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.47 g, 2.493 mmol) in methanol (30 mL). The mixture was heated to reflux for 5 h before the solvent was removed under reduced pressure. The residue was acidified to pH 5-6 with 2N HCl, and the mixture was allowed to stand overnight at room temperature. The solvent was collected by filtration, washed with water, and dried via azeotrope with benzene to give 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.69 g, 48% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.57 (d, J=1.51 Hz, 1H), 8.09-8.15 (m, 3H), 7.91 (d, J=7.53 Hz, 1H), 7.80 (d, J=7.78 Hz, 1H), 7.69 (t, J=7.65 Hz, 1H), 3.51 (s, 2H), 3.28 (s, 3H), 2.48 (br. s., 2H), 2.33 (br. s., 4H), 2.04 (br. s., 1H), 1.84 (t, J=11.29 Hz, 2H), 1.43 (br. s., 6H), 1.29-1.38 (m, 2H), 0.95-1.11 (m, 2H); MS (m/z) 576.2 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h before the solvent
  3. customwas removed under reduced pressure
  4. filtrationThe solvent was collected by filtration
  5. washwashed with water
  6. dry with materialdried via azeotrope with benzene

Sources & evidence

ORD record
ord-8a0a3307e2f54848a3bf82456e264852
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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