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

HRID 245255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245255
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 674171446-(Methylsulfonyl)-3-[(4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 126,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b558e278d514437ca38d018a7b9ebbf0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

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