Triethylamine → HCID 178493100, Verbindung

HRID 2076060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076060
Cl.C(O[C:5]([CH:7]1[C:12](=O)[CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][N:9]([CH3:20])[CH2:8]1)=[O:6])C.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH:43][C:44]([NH2:46])=[NH:45])[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([NH:43][C:44]2[N:46]=[C:5]([OH:6])[C:7]3[CH2:8][N:9]([CH3:20])[CH2:10][CH:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:12]=3[N:45]=2)[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 242006311-Methyl-4-oxo-5-phenyl-piperidine-3-carboxylic acid ethyl ester hydrochlorideHCID 178493228HCID 178493228, Verbindung

Produkt 1

HCID 178493100HCID 178493100, VerbindungAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

A mixture of 1-methyl-4-oxo-5-phenyl-piperidine-3-carboxylic acid ethyl ester hydrochloride (89 mg, 0.3 mmol), N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (111 mg, 0.33 mmol), and triethylamine (0.21 mL, 1.5 mmol) in ethanol (2 mL) was heated at 78° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (40 mL), and then washed with saturated aqueous sodium carbonate solution (10 mL) and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by column chromatography on silica gel using ethyl acetate/0-30% ethanol as eluent to give the title compound (43 mg, 32%) as a brown solid (from ethyl acetate/cyclohexane). MS ISP (m/e): 443.5 [(M+H)+]. mp 152-155° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. washwashed with saturated aqueous sodium carbonate solution (10 mL) and with brine (10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual material was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-70dd0ff49c0d415a8f1ec38483f10bd7
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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