Hexane → 2-(3-oxocyclohexyl)-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide

HRID 888267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888267
ClC(N(C)C)=C(C)C.[O:9]=[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][C:17]([OH:19])=O)[CH2:11]1.[F:20][C:21]([F:42])([F:41])[C:22]1[CH:23]=[C:24]([S:28]([CH2:31][CH2:32][S:33][C:34]2[C:39]([NH2:40])=[CH:38][CH:37]=[CH:36][N:35]=2)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1.CCCCCC>C(Cl)Cl.O>[O:9]=[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([CH2:16][C:17]([NH:40][C:39]2[C:34]([S:33][CH2:32][CH2:31][S:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:41])([F:42])[F:20])[CH:23]=3)(=[O:30])=[O:29])=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:19])[CH2:11]1

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 37268152-(3-Oxocyclohexyl)acetic acidHCID 67133713[2-[2-[[3-(Trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine

Produkt 1

HCID 469178832-(3-oxocyclohexyl)-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

560 μl (4.23 mmol) 1-chloro-N,N,2-trimethylprop-1-en-1-amine were added at 0° C. to a solution of 550 mg (35.2 mmol) 2-(3-oxocyclohexyl)acetic acid in DCM (7 ml). After stirring for 15 min at 0° C., 1.5 g (4.23 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) were added. Then the reaction solution was stirred for a further 16 h at 0° C. It was then diluted with water (30 ml) and extracted with DCM (3×50 ml). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 6:4) of the residue yielded 220 mg (0.44 mmol, 13%) 2-(3-oxocyclohexyl)-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide. MS: m/z 501.1 [M+H]+.

Aufarbeitung

  1. stirringThen the reaction solution was stirred for a further 16 h at 0° C
  2. extractionextracted with DCM (3×50 ml)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6333aba2bb514cbd9365e64a3d594b06
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247573B2

Notizen zur Reaktion

Wird geladen…