Sodium hydride → N-Methoxy-N-methyl-3-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionamide

HRID 1096253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096253
[H-].[Na+].[CH3:3][CH:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:20])([F:19])[F:18])[CH:11]=2)[CH2:8][CH2:7][NH:6][C:5]1=[O:21].Br[CH2:23][CH2:24][C:25]([N:27]([O:29][CH3:30])[CH3:28])=[O:26]>CN(C)C=O>[CH3:30][O:29][N:27]([CH3:28])[C:25](=[O:26])[CH2:24][CH2:23][N:6]1[CH2:7][CH2:8][N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:20])([F:19])[F:18])[CH:11]=2)[CH:4]([CH3:3])[C:5]1=[O:21]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 112063733-bromo-N-methoxy-N-methylpropanamideHCID 667830063-Methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one

Produkt 1

HCID 86638390N-Methoxy-N-methyl-3-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-propionamideAusbeute 105,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (55% dispersion in mineral oil, 24 mg, 0.56 mmol) was added at 0° C. to a solution of 3-methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one (example 41D; 127 mg, 0.46 mmol) in N,N-dimethylformamide (3 mL), then after 5 min a solution of 3-bromo-N-methoxy-N-methyl-propionamide (Patent Application US 2007249589; 100 mg, 0.51 mmol) was added. After 30 min the ice bath was removed and the reaction mixture was allowed to reach RT over 1 h, then partitioned between EtOAc and 10% aq. KHSO4 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (189 mg) which was directly used in the next step. Light yellow oil, MS: 390.3 (M+H)+.

Aufarbeitung

  1. customAfter 30 min the ice bath was removed
  2. custompartitioned between EtOAc and 10% aq. KHSO4 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-db71a29879934dcc8430fcbf813b79c3
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138175B2

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