Cesium carbonate → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-6-{[2-(propylamino)ethyl]amino}-1,2-benzisothiazole-3-carboxamide

HRID 449999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449999
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P([C:41]2[CH:46]=[CH:45]C=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65](Br)=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2.C(=O)([O-])[O-].[Cs+].[Cs+].N1CCCC1=O.C[N:81]1[CH2:85][CH2:84][NH:83]C1=O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:47]12[CH2:54][CH2:53][CH:50]([CH2:51][CH2:52]1)[C@H:49]([NH:55][C:56]([C:58]1[C:62]3[CH:63]=[CH:64][C:65]([NH:81][CH2:85][CH2:84][NH:83][CH2:45][CH2:46][CH3:41])=[CH:66][C:61]=3[S:60][N:59]=1)=[O:57])[CH2:48]2

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 10044409HCID 10044409, VerbindungHCID 672293681-Methyl-2-imidazolidinone 2-pyrrolidinone

Produkt 1

HCID 67230658N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-6-{[2-(propylamino)ethyl]amino}-1,2-benzisothiazole-3-carboxamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Palladium (II) acetate (0.09 mmol) was added to a solution of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.14 mmol) in toluene (8 mL) and the reaction mixture was maintained until the contents completely dissolved. The resultant yellow solution was transferred to a mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (0.33 mmol), cesium carbonate (0.39 mmol) and 1-methyl-2-imidazolidinone 2-pyrrolidinone (0.500 mmol) under an atmosphere of nitrogen gas and the reaction mixture was heated at 100° C. for 16 h. The reaction mixture was filtered through Celite and concentrated. The residue was purified by HPLC, thus providing the product in 70% yield.

Aufarbeitung

  1. temperaturethe reaction mixture was maintained until the contents
  2. dissolutioncompletely dissolved
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC
  6. customthus providing the product in 70% yield

Quellen und Nachweise

ORD-Eintrag
ord-1030cd2aa73f4544a5c7107d88eb0b2f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486937B2

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