Triethylamine → HCID 68586366, Verbindung

HRID 17495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17495
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[C:9]([N:12]([CH3:38])[CH2:13][CH2:14][N:15]([CH3:37])[C:16]([C:18]1[O:19][C:20]2[C:26](F)=[C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]([CH3:34])=[C:23]([C:35]#[N:36])[C:21]=2[N:22]=1)=[O:17])(=[O:11])[CH3:10].C(N(CC)CC)C>CS(C)=O>[C:9]([N:12]([CH3:38])[CH2:13][CH2:14][N:15]([CH3:37])[C:16]([C:18]1[O:19][C:20]2[C:26]([N:5]3[CH2:6][CH2:7][C@H:3]([N:2]([CH3:8])[CH3:1])[CH2:4]3)=[C:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:24]([CH3:34])=[C:23]([C:35]#[N:36])[C:21]=2[N:22]=1)=[O:17])(=[O:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68584367N-{2-[acetyl(methyl)amino]ethyl}-4-cyano-N,5-dimethyl-7-fluoro-6-phenyl-1,3-benzoxazole-2-carboxamide

Produkt 1

HCID 68586366HCID 68586366, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

Under nitrogen atmosphere at 140 to 150° C., a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidin (32 μl, 256 μmol) was added to a dimethyl sulfoxide (3 ml) solution of N-{2-[acetyl(methyl)amino]ethyl}-4-cyano-N,5-dimethyl-7-fluoro-6-phenyl-1,3-benzoxazole-2-carboxamide (I-204) (87 mg, 213 μmol) and triethylamine (39 μl, 277 μmol), followed by stirring at the same temperature for 45 minutes. After cooling, the solvent was evaporated away under reduced pressure, the residue was dissolved in chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (10:1, v/v) gave the entitled compound (47 mg, 44%) as an amorphous substance.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe solvent was evaporated away under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a770d49a28e4442b8622c5d5786b9982
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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