Morpholine → HCID 59506284, Verbindung

HRID 1098763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098763
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([Br:13])[CH:5]=1)(=[O:3])[CH3:2].[B-](F)(F)(F)F.[CH3:19][CH2:20][O:21][C:22]([C:24](C#N)=[N:25]OC(N(C)C)=[N+](C)C)=O.N1CCOCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:13][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:12]=[CH:11][C:7]=1[C:8]([N:25]1[CH2:19][CH2:20][O:21][CH2:22][CH2:24]1)=[O:10]

Komponenten

8

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 13347277HCID 13347277, Verbindung

Produkt 1

HCID 59506284HCID 59506284, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the product obtained in step 3 (230 mg, 0.95 mmol) and TOTU (310 mg, 0.95 mmol) in DMF (2 mL) was added morpholine (83 μL, 0.95 mmol) and DIPEA (162 μL, 0.95 mmol). The reaction mixture was stirred for 2 h at RT. Ethyl acetate (20 ml) and water (20 ml) was added, the organic phase was separated and washed with hydrochloric acid (1 M, 20 ml), water (20 ml), brine (2×20 ml) and dried over Na2SO4. After evaporation and flash-chromatography the product was obtained as oil (160 mg, 54%).

Aufarbeitung

  1. customthe organic phase was separated
  2. washwashed with hydrochloric acid (1 M, 20 ml), water (20 ml), brine (2×20 ml)
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation and flash-chromatography the product

Quellen und Nachweise

ORD-Eintrag
ord-4c95c90a1d6e4051abd9ed8da27e600a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143242B2

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