Hydrochloric Acid → 5-Acetyl-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1888805Notes

Reaction equation

HRID 1888805 reaction equation
Cl.C([O:6][C:7]([C:9]1[CH:10]=[C:11]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[O:28])[C:12](=[O:26])[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:14]=1[CH3:15])=[CH2:8])CCC.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:7]([C:9]1[CH:10]=[C:11]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[O:28])[C:12](=[O:26])[N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:14]=1[CH3:15])(=[O:6])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 667254565-(1-Butoxyvinyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 667252635-Acetyl-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Aqueous hydrochloric acid (2.0M, 50 μl) was added to a solution of 5-(1-butoxyvinyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (38 mg, 67.5 μmol) in DMF (0.5 ml). After 20 min. the solution was neutralized with aqueous sodium hydrogen carbonate. The reaction mixture was purified by preparative HPLC to give the title compound as a white solid (17.6 mg, 51%).

Workup

  1. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-442e58c1403b4e29bc85de15e580d764
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

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