Morpholine → HCID 69292803, Verbindung

HRID 747579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747579
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:53][O:54][C:55]([C:57]1[S:58][C:59]([C:62](=[O:73])[NH:63][C@@H:64]([C:66]2[CH:71]=[CH:70][C:69](Br)=[CH:68][CH:67]=2)[CH3:65])=[CH:60][CH:61]=1)=[O:56].[NH:74]1[CH2:79][CH2:78][O:77][CH2:76][CH2:75]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:53][O:54][C:55]([C:57]1[S:58][C:59]([C:62](=[O:73])[NH:63][C@@H:64]([C:66]2[CH:71]=[CH:70][C:69]([N:74]3[CH2:79][CH2:78][O:77][CH2:76][CH2:75]3)=[CH:68][CH:67]=2)[CH3:65])=[CH:60][CH:61]=1)=[O:56]

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 11537926HCID 11537926, Verbindung

Produkt 1

HCID 69292803HCID 69292803, VerbindungAusbeute 7,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a suspension of 1.0 mg (0.0045 mmol) palladium(II) acetate, 4.06 mg (0.0065 mmol) 2,2′-bis-(diphenylphosphino)-1,1′-binaphtyl (BINAP) and 125 mg (0.384 mmol) cesium carbonate in 1 ml dry toluene, 100 mg (0.272 mmol) (R)-5-[1-(4-Bromo-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester (see example 1, step 1) and 30.0 mg (0.344 mmol) morpholine were added under an argon atmosphere. The mixture was heated in the microwave oven (Emrys Optimizer) at 160° C. for 15 min. After cooling to room temperature, the reaction mixture was filtered and the solid was washed with toluene. The solvent of the combined filtrates was evaporated and the crude product purified by preparative HPLC to yield 7.9 mg (0.021 mmol) (R)-5-[1-(4-Morpholin-4-yl-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester.

Aufarbeitung

  1. additionwere added under an argon atmosphere
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washthe solid was washed with toluene
  5. customThe solvent of the combined filtrates was evaporated
  6. customthe crude product purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-23b3fe28301b4fec88659e7c6d9406b4
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396944B2

Notizen zur Reaktion

Wird geladen…