Sodium Iodide → n-Cyclohexyl-2-(6-methyl-6-{3-[(methylsufonyl)amino]phenyl}-3-azabicyclo[3.1.0]hex-3-yl)acetamide

HRID 428869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428869
[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:7]2[CH:3]1[CH2:4][NH:5][CH2:6]2.C(=O)([O-])O.[Na+].Cl[CH2:25][C:26]([NH:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:27].[I-].[Na+]>CN(C)C=O.O.C(OCC)C>[NH3:5].[CH:29]1([NH:28][C:26](=[O:27])[CH2:25][N:5]2[CH2:6][CH:7]3[CH:3]([C:2]3([CH3:1])[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=3)[CH2:4]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Komponenten

9

Edukt 4

HCID 5238Sodium IodideHCID 2223652-Chloro-N-cyclohexylacetamideHCID 516892Sodium BicarbonateHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

Produkt 2

HCID 222AmmoniaHCID 22141352n-Cyclohexyl-2-(6-methyl-6-{3-[(methylsufonyl)amino]phenyl}-3-azabicyclo[3.1.0]hex-3-yl)acetamideAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 57 mg, 0.19 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (630 mg, 7.52 mmol), 2-chloro-N-cyclohexylacetamide (36 mg, 0.2 mmol) and sodium iodide (catalytic) and the reaction was heated at 50° C. for 20 h. After cooling diethyl ether (5 ml) and water (7 ml) were added and the reaction mixture was stirred vigorously for 5 min. The phases were separated and the aqueous layer was further extracted with diethyl ether (2×5 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residual oil was purified by flash column chromatography using a Sep-Pak™ cartridge packed with silica gel (5 g) eluting with dichloromethane:ethanol:0.88 ammonia solution (200:8:1) to afford the title compound as an oil (22 mg, 28%).

Aufarbeitung

  1. additionwere added
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with diethyl ether (2×5 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by flash column chromatography
  8. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a6d729ad0be44e8b813b00505099e9be
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313312B1

Notizen zur Reaktion

Wird geladen…