Dichloromethane → N-(2-thienylmethyl)-2-[2-[3-(trifluoromethyl)-phenyl]sulfonylethylthio]-3-quinoline carboxamide

HRID 1949171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949171
C([O-])([O-])=O.[K+].[K+].Cl[CH2:8][CH2:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)(=[O:12])=[O:11].[SH:23][C:24]1[C:33]([C:34]([NH:36][CH2:37][C:38]2[S:39][CH:40]=[CH:41][CH:42]=2)=[O:35])=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1.C(Cl)Cl>CC(C)=O>[S:39]1[CH:40]=[CH:41][CH:42]=[C:38]1[CH2:37][NH:36][C:34]([C:33]1[C:24]([S:23][CH2:8][CH2:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)(=[O:12])=[O:11])=[N:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:35]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27365062-Chloroethyl-[3-(trifluoromethyl)phenyl]sulphoneHCID 178523047HCID 178523047, Verbindung

Produkt 1

HCID 46911643N-(2-thienylmethyl)-2-[2-[3-(trifluoromethyl)-phenyl]sulfonylethylthio]-3-quinoline carboxamideAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

151 mg (1.1 mmol) K2CO3 and 300 mg (1.1 mmol) 1-(2-chloroethylsulfonyl)-3-(trifluoromethyl)benzene were added to a solution of 300 mg (1.0 mmol) 2-mercapto-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV02) in acetone (10 ml) at RT and the mixture was heated for 3 h at 70° C. Then it was filtered and the filtrate was concentrated to small volume under vacuum. The residue was taken up with EE and washed with water and brine, dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (DCM/EE 20:1) of the residue yielded 163 mg (0.3 mmol, 30%) N-(2-thienylmethyl)-2-[2-[3-(trifluoromethyl)-phenyl]sulfonylethylthio]-3-quinoline carboxamide. MS: m/z 537.1 [M+H]+.

Aufarbeitung

  1. filtrationThen it was filtered
  2. concentrationthe filtrate was concentrated to small volume under vacuum
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b12696f819e043679217a6db1f51d0f6
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399673B2

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