Trifluoromethanesulfonic acid → 5-Iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoro-methyl)phenyl]1,2-dihydropyridine-3-carboxamide

HRID 1888790

Reaktionsgleichung

Reaktionsgleichung von HRID 1888790
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.[I:41]N1C(=O)CCC1=O>CC#N.C(Cl)Cl>[I:41][C:3]1[CH:4]=[C:5]([C:19]([NH:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=2)=[O:20])[C:6](=[O:18])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)[C:2]=1[CH3:1]

Komponenten

6

Edukt 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 116196256-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Produkt 1

HCID 115199335-Iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoro-methyl)phenyl]1,2-dihydropyridine-3-carboxamideAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (200 mg, 0.43 mmol) in MeCN (1.5 ml) at room temperature and under argon was added trifluoromethanesulfonic acid (1 ml) followed by N-iodosuccinimide (97 mg, 0.43 mmol). After 45 min, the reaction mixture was diluted with DCM, washed with aqueous NaHCO3, with aqueous NaS2O4 and water, dried (Na2SO4), and evaporated to give the title compound (200 mg).

Aufarbeitung

  1. washwashed with aqueous NaHCO3, with aqueous NaS2O4 and water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f7746aec86ba4b0d89cc4ea9936c48b5
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501784B2

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