Sodium Hydroxide → 6-[(1-Methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245222

Reaktionsgleichung

Reaktionsgleichung von HRID 245222
[OH-].[Na+].[CH3:3][CH:4]([S:6]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:13]([CH2:29][N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH:32]([CH3:37])[CH2:31]1)=[C:12]2[C:38]([O:40]C)=[O:39])(=[O:8])=[O:7])[CH3:5]>CO.O1CCCC1>[CH3:5][CH:4]([S:6]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:13]([CH2:29][N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH:32]([CH3:37])[CH2:31]1)=[C:12]2[C:38]([OH:40])=[O:39])(=[O:7])=[O:8])[CH3:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 67416594Methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Produkt 1

HCID 674172316-[(1-Methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium hydroxide (11.02 mL of a 2M solution, 22.04 mmol) was added to a yellow solution of methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.24 g, 2.204 mmol) in methanol (11.02 mL) and tetrahydrofuran (11.02 mL). The mixture was heated to 50° C. for 20 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was diluted with water (5 mL), and the solid precipitate was collected by filtration, washed with water (2×1 mL), and dried in a vacuum oven at 40° C. to afford 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.95 g, 72% yield). 1H NMR (400 MHz, DMSO-d6) δ8.53 (d, J=1.76 Hz, 1H), 8.10-8.18 (m, 2H), 7.96-8.05 (m, 2H), 7.83 (d, J=7.81 Hz, 1H), 7.72 (t, J=7.68 Hz, 1H), 3.71 (s, 2H), 3.49 (dt, J=6.77, 13.41 Hz, 1H), 2.68-2.78 (m, 2H), 2.08-2.32 (m, 3H), 1.92-2.03 (m, 2H), 1.22 (s, 3H), 1.20 (s, 3H), 0.70 (d, J=6.55 Hz, 3H); MS (m/z) 549.2 (M+H+).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with water (5 mL)
  4. filtrationthe solid precipitate was collected by filtration
  5. washwashed with water (2×1 mL)
  6. customdried in a vacuum oven at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-e985ab1600e044dbb70109b4ac8d0f32
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658636B2

Verknüpfte Notizen

Wird geladen…