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

HRID 559808Notes

Reaction equation

HRID 559808 reaction equation
Br[CH:2]([CH3:37])[C:3]([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:38]([NH2:41])(=[O:40])[CH3:39].C1(C)C(C)=CC=CC=1.OS(O)(=O)=O>O.CC#N>[CH3:39][C:38]1[O:40][C:2]([CH3:37])=[C:3]([C:5]2[CH:6]=[C:7]([C:23]([NH:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:31][CH:32]=3)=[O:24])[C:8](=[O:22])[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[C:10]=2[CH3:11])[N:41]=1

Participants

7

Reactant 4

HCID 178AcetamideHCID 1118Sulfuric AcidHCID 7237O-XyleneHCID 866147825-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 667253385-(2,5-Dimethyl-1,3-oxazol-4-yl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 36.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(2-bromopropanoyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (130 mg, 0.22 mmol), acetamide (262 mg, 4.4 mmol), xylene (300 μl) and conc. H2SO4 (10 μl) was heated with stirring for 2 h. The reaction was diluted with water and CH3CN and purified on preparative HPLC, affording the title compound (45 mg, 36%).

Workup

  1. temperaturewas heated
  2. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-8abbd07ec4034074a0e8854302f6fcd3
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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