Acetamide → 6-Methyl-5-(2-methyl-1,3-oxazol-4-yl)-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1888807

Reaktionsgleichung

Reaktionsgleichung von HRID 1888807
BrCC([C:5]1[CH:6]=[C:7]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:8](=[O:22])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]=1[CH3:11])=O.[C:37]([NH2:40])(=[O:39])[CH3:38].[C:41]1(C)C(C)=CC=C[CH:46]=1.OS(O)(=O)=O>O.CC#N>[CH3:11][C:10]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[C:8](=[O:22])[C:7]([C:23]([NH:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=2)=[O:24])=[CH:6][C:5]=1[C:41]1[N:40]=[C:37]([CH3:38])[O:39][CH:46]=1

Komponenten

7

Edukt 4

HCID 178AcetamideHCID 1118Sulfuric AcidHCID 7237O-XyleneHCID 866147805-(bromoacetyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Produkt 1

HCID 667253196-Methyl-5-(2-methyl-1,3-oxazol-4-yl)-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5-(bromoacetyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (90 mg, 0.15 mmol) and acetamide (44 mg, 0.75 mmol), xylene (300 μl) and cone. H2SO4 (10 μl) was heated with stirring for 3 h. The reaction was diluted with water and CH3CN and purified on preparative HPLC affording the title compound (37 mg, 45%).

Aufarbeitung

  1. custompurified on preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ef86b537969447e1b550c89bb058db9e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501784B2

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