Potassium Hydroxide → 3-(1,4'-Bipiperidin-1'-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245162Notes

Reaction equation

HRID 245162 reaction equation
[OH-].[K+].[N:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[C:17]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=4)=[N:18][C:19]4[C:24]([C:25]=3[C:26]([O:28]C)=[O:27])=[CH:23][C:22]([S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])=[C:21]([O:35][CH3:36])[CH:20]=4)[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[K]>CO.O>[N:3]1([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[C:17]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:44])([F:46])[F:45])[CH:38]=4)=[N:18][C:19]4[C:24]([C:25]=3[C:26]([OH:28])=[O:27])=[CH:23][C:22]([S:30]([CH2:33][CH3:34])(=[O:32])=[O:31])=[C:21]([O:35][CH3:36])[CH:20]=4)[CH2:13][CH2:14]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 71183031Methyl 3-(1,4'-bipiperidin-1'-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 674173713-(1,4'-Bipiperidin-1'-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Potassium hydroxide (1.86 g, 33.1 mmol) was added to a solution of methyl 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.1 g, 3.31 mmol) in methanol (60 mL) and water (20 mL). The mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and diluted with water. The methanol was removed in vacuo. The solid precipitate was collected by filtration, washed with cold water, and air dried to afford 3-(1,4′-bipiperidin-1′-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.0 g, 92% yield) as the potassium salt. 1H NMR (400 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.11 (s, 1H), 7.91 (d, J=7.78 Hz, 1H), 7.79 (d, J=7.78 Hz, 1H), 7.67 (t, J=7.78 Hz, 1H), 7.55 (s, 1H), 4.04 (s, 3H), 3.42-3.52 (m, 4H), 2.33 (br. s., 4H), 2.03 (t, J=11.80 Hz, 1H), 1.82 (t, J=11.29 Hz, 2H), 1.39-1.48 (m, 6H), 1.30-1.39 (m, 2H), 1.12 (t, J=7.40 Hz, 3H), 0.97-1.09 (m, 2H); MS (m/z) 620.2 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe methanol was removed in vacuo
  4. filtrationThe solid precipitate was collected by filtration
  5. washwashed with cold water, and air
  6. customdried

Sources & evidence

ORD record
ord-c0396f9c87884dcb9b03049dc23d269f
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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