Potassium Hydroxide → 6-(Ethylsulfonyl)-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245168Notes

Reaction equation

HRID 245168 reaction equation
[OH-].[K+].[CH2:3]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:12]([CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]1)=[C:11]2[C:43]([O:45]C)=[O:44])(=[O:7])=[O:6])[CH3:4].[K]>CO.O>[CH2:3]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:12]([CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[CH2:33][CH2:32]1)=[C:11]2[C:43]([OH:45])=[O:44])(=[O:7])=[O:6])[CH3:4]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 67417221Methyl 6-(ethylsulfonyl)-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 674174906-(Ethylsulfonyl)-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 102.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Potassium hydroxide was added to a solution of methyl 6-(ethylsulfonyl)-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.0 g, 3.15 mmol) in methanol (60 mL) and water (20 mL) and reaction mixture was heated to reflux overnight. The mixture was cooled to room temperature and diluted with water. The methanol was removed under reduced pressure. The solid was collected by filtration, washed with cold water, and air dried to afford 6-(ethylsulfonyl)-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.0 g, 96% yield) as the potassium salt. 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 1H), 8.13 (s, 1H), 7.92 (d, J=7.53 Hz, 1H), 7.79 (d, J=7.78 Hz, 1H), 7.68 (t, J=7.78 Hz, 1H), 7.55 (s, 1H), 4.04 (s, 3H), 3.49-3.55 (m, 4H), 3.43-3.49 (m, 4H), 2.53-2.57 (m, 2H), 2.33-2.38 (m, 4H), 1.93-2.04 (m, 1H), 1.84 (t, J=11.04 Hz, 2H), 1.52 (d, J=11.29 Hz, 2H), 1.12 (t, J=7.28 Hz, 3H), 0.95-1.08 (m, 2H); MS (m/z) 622.2 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe methanol was removed under reduced pressure
  4. filtrationThe solid was collected by filtration
  5. washwashed with cold water, and air
  6. customdried

Sources & evidence

ORD record
ord-d9bc8d177bb3490489083752392cb3f4
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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