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

HRID 559804

Reaction equation

HRID 559804 reaction equation
Br[CH2:2][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.[CH:37]([NH2:39])=[O:38].C1(C)C(C)=CC=CC=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:20])([F:21])[F:19])[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:35])=[O:34])=[CH:31][CH:32]=2)=[O:24])=[CH:6][C:5]=1[C:3]1[N:39]=[CH:37][O:38][CH:2]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 1118Sulfuric AcidHCID 7237O-XyleneHCID 866147805-(bromoacetyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 667252956-Methyl-N-[4-(methylsulfonyl)benzyl]-5-(1,3-oxazol-4-yl)-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-(bromoacetyl)-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (Example 50 (c), 100 mg, 0.17 mmol), formamide (135 μl, 3.4 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 (23 mg, 31%).

Workup

  1. temperaturewas heated
  2. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-22221aa67f0245a0a1ae3bad442dde9c
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Linked notes

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