Sodium Bicarbonate → HCID 178456892, Verbindung

HRID 1620512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620512
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:13][CH:12]2[CH2:14][CH:8]([CH2:9][CH:10]([CH:15]=O)[CH2:11]2)[CH2:7]1.[CH2:27]([NH:30][C:31]1[CH2:35][S:34][C:33](=[O:36])[N:32]=1)[C:28]#[CH:29].C([O-])(=O)C.[NH2+]1CCCCC1.C(=O)([O-])O.[Na+]>CC(O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:4]=1[CH2:5][N:6]1[CH2:7][CH:8]2[CH2:14][CH:12]([CH2:11][CH:10](/[CH:15]=[C:35]3/[C:31]([NH:30][CH2:27][C:28]#[CH:29])=[N:32][C:33](=[O:36])[S:34]/3)[CH2:9]2)[CH2:13]1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 3014295Piperidinium acetateHCID 866787043-[2,4-Bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehydeHCID 178456890HCID 178456890, Verbindung

Produkt 1

HCID 178456892HCID 178456892, VerbindungAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-[2,4-bis(trifluoromethyl)benzyl]-3-azabicyclo[3.3.1]nonane-7-carbaldehyde (173.9 mg) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (141 mg) in 2-propanol (2.29 mL) was added piperidinium acetate (66.6 mg). The reaction mixture was stirred at 60° C. overnight, allowed to cool to room temperature, poured into saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/hexane to give the title compound (36.4 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-31d68afab5d34402b880e415b0d602da
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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