2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → 4-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromide

HRID 1910518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910518
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[Br:26][CH2:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[O:29]>CCOC(C)=O>[Br-:26].[F:25][C:21]1[CH:20]=[C:19]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[O:10][C:8]([CH:5]2[CH2:4][CH2:3][N+:2]([CH3:1])([CH2:27][C:28](=[O:29])[C:30]3[S:31][CH:32]=[CH:33][N:34]=3)[CH2:7][CH2:6]2)=[O:9])[CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 70925814Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate

Produkt 1

HCID 866729524-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromideAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate (106 mg, 0.31 mmol, prepared as in example 40) in EtOAc (3 ml), 2-bromo-1-(thiazol-2-yl)ethanone (63.2 mg, 0.31 mmol) was added. The mixture was stirred at room temperature for 27 hours. The solvent was evaporated, and the crude was triturated with Et2O and collected by filtration. The compound was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain 4-((bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromide (120 mg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O
  3. filtrationcollected by filtration
  4. customThe compound was purified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-7cc09076f07d416795c1f1b750386435
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604015B2

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