Methanol → 6-(Methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245255Notes

Reaction equation

HRID 245255 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1)[C:9]([CH2:25][N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)=[C:8]2[C:33]([O:35]C)=[O:34])(=[O:4])=[O:3].[OH-].[Na+].CO>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=1)[C:9]([CH2:25][N:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1)=[C:8]2[C:33]([OH:35])=[O:34])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67417193Methyl 6-(methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 674171446-(Methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 126.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-(methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (0.796 g, 1.529 mmol) and 3N NaOH (5.097 mL, 15.29 mmol) were suspended in tetrahydrofuran (5.097 mL) and methanol (5.097 mL) and heated to 50° C. for 20 h. The tetrahydrofuran and methanol were removed under reduced pressure, and the residue was diluted with water. The mixture was purified via Oasis SPE cartridge to afford 6-(methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.977 g). This material was used without further purification. MS (m/z) 507.2 (M+H+).

Workup

  1. customThe tetrahydrofuran and methanol were removed under reduced pressure
  2. additionthe residue was diluted with water
  3. customThe mixture was purified via Oasis SPE cartridge

Sources & evidence

ORD record
ord-b558e278d514437ca38d018a7b9ebbf0
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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