p-Toluenesulfonic acid monohydrate → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-(3-chlorophenyl)-1,3-oxazole-2-carboxamide 4-methylbenzenesulfonate

HRID 1359651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359651
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][C:11]([C:13]([O:15]CC)=O)=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:18][C@@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>CCO>[CH3:38][C:28]1[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:32][CH:33]=1.[N:21]12[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22]1)[C@@H:19]([NH:18][C:13]([C:11]1[O:12][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[CH:9][N:10]=1)=[O:15])[CH2:20]2

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amineHCID 22350710Ethyl 5-(3-chlorophenyl)oxazole-2-carboxylate

Produkt 1

HCID 86584883N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-(3-chlorophenyl)-1,3-oxazole-2-carboxamide 4-methylbenzenesulfonateAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of the product from Step 79c (0.419 g, 1.66 mmol, 1.0 eq), (R)-(+)-3-aminoquinuclidine (0.221 g, 1.75 mmol, 1.05 eq) and EtOH (4.0 mL) is heated under reflux. After 64 h, the mixture is cooled and the contents are filtered through glass wool into p-toluenesulfonic acid monohydrate (0.315 g, 1.65 mmol, 1.0 eq). The resulting solid is filtered and dried in vacuo to afford the title compound (0.59 g, 65%). HRMS (FAB) calculated for C17H18ClN3O2+Hl 332.1165, found 332.1180.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturethe mixture is cooled
  4. filtrationThe resulting solid is filtered
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2189893c9c134ec6af186065e4b1e58e
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599916B2

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