1,1'-Carbonyldiimidazole → 2-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamide

HRID 660056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660056
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([OH:29])=O)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:37]=[C:38]([CH:42]([NH2:44])[CH3:43])[CH:39]=[CH:40][CH:41]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[C:13]1([S:19]([CH2:22][CH2:23][S:24][C:25]2[N:33]=[CH:32][CH:31]=[CH:30][C:26]=2[C:27]([NH:44][CH:42]([C:38]2[CH:39]=[CH:40][CH:41]=[C:36]([C:35]([F:34])([F:45])[F:46])[CH:37]=2)[CH3:43])=[O:29])(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 2782448(1R)-1-(3-(Trifluoromethyl)phenyl)ethylamineHCID 28213502-[2-(Phenylsulfonyl)ethylthio]nicotinic acidHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 252215192-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

264 mg (1.62 mmol) of CDI were added to a solution of 500 mg (1.55 mmol) of 2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DCM (12 ml), and the mixture was stirred for 1 h at RT. A solution of 292 mg (1.55 mmol) of 1-(3-(trifluoromethyl)phenyl)ethylamine in DCM (12 ml) was then added, and stirring was continued for a further 16 h at RT. The reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. CC with the residue (ethyl acetate/hexane 1:1) yielded 462 mg (0.93 mmol, 60%) of 2-(2-(phenylsulfonyl)ethylthio)-N-(1-(3-(trifluoromethyl)phenyl)ethyl)nicotinamide. MS: m/z 495.1 [M+H]+.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for a further 16 h at RT
  3. washThe reaction solution was then washed in each case three times with sat. aq. ammonium chloride solution and saturated aqueous NaCl solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-90994e99c2244041a6db803193f84607
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084470B2

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