Potassium Hydroxide → HCID 67417500, compound

HRID 245233Notes

Reaction equation

HRID 245233 reaction equation
[OH-].[K+].[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:11]([CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH2:30][CH2:29]1)=[C:10]2[C:40]([O:42]C)=[O:41])(=[O:6])=[O:5]>CO.O>[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1)[C:11]([CH2:27][N:28]1[CH2:29][CH2:30][CH:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[CH2:32][CH2:33]1)=[C:10]2[C:40]([OH:42])=[O:41])(=[O:6])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67418114HCID 67418114, compound

Product 1

HCID 67417500HCID 67417500, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (1.42 g, 25.4 mmol) was added to a solution of methyl 6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (3.0 g, 5.07 mmol) in methanol (60 mL) and water (20 mL), and the resulting mixture was heated to reflux for 5 h. The solvent was removed under reduced pressure, and the residue was adjusted to pH˜5-6 with 2N HCl and extracted with methylene chloride (three times). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (2.73 g, 81% yield). MS (m/z) 578.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-2ded77128e984ad8afdcce58b1079826
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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