Potassium Hydroxide → HCID 67418827, compound

HRID 245218Notes

Reaction equation

HRID 245218 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:39]([O:41]C)=[O:40])=[C:11]([CH2:26][N:27]3[CH2:32][CH2:31][CH:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:29][CH2:28]3)[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)=[N:13]2)=[CH:8][C:7]=1[S:43]([CH2:46][CH3:47])(=[O:45])=[O:44])[CH3:4]>CO.O>[CH2:3]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:39]([OH:41])=[O:40])=[C:11]([CH2:26][N:27]3[CH2:28][CH2:29][CH:30]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)[CH2:31][CH2:32]3)[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=3)=[N:13]2)=[CH:8][C:7]=1[S:43]([CH2:46][CH3:47])(=[O:45])=[O:44])[CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67418349HCID 67418349, compound

Product 1

HCID 67418827HCID 67418827, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Potassium hydroxide (1.805 g, 32.2 mmol) was added to a solution of methyl 7-(ethyloxy)-6-(ethylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.09 g, 3.22 mmol) in methanol (60 mL) and water (20 mL). The mixture was heated to reflux overnight, cooled to room temperature, and diluted with water. The methanol was removed under reduced pressure, and the remaining aqueous solution was acidified to pH 6 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo to afford 7-(ethyloxy)-6-(ethylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (1.82 g, 89% yield). 1H NMR (400 MHz, DMSO-d6) ™ 8.80 (s, 1H), 8.03 (s, 1H), 7.88-7.94 (m, 2H), 7.76-7.82 (m, 1H), 7.67 (s, 1H), 4.37 (q, J=6.94 Hz, 2H), 4.08 (br. s., 2H), 3.50-3.62 (m, 6H), 2.99 (br. s., 2H), 2.31-2.59 (m, 6H), 1.79 (d, J=12.30 Hz, 2H), 1.45 (t, J=6.90 Hz, 3H), 1.23-1.41 (m, 3H), 1.14 (t, J=7.40 Hz, 3H); MS (m/z) 636.2 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe methanol was removed under reduced pressure
  4. extractionextracted with methylene chloride (three times)
  5. washThe combined organic extracts were washed with brine (two times)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6680086ba22244c5ae2b9ed8737b7f17
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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