Triethylamine → 6-cyano-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinolinecarboxamide

HRID 1259853

Reaktionsgleichung

Reaktionsgleichung von HRID 1259853
C1C=CC2N(O)N=NC=2C=1.C(N=C=NCCCN(C)C)C.[C:22]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[C:29]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:28]=[C:27]2[C:40](O)=[O:41])#[N:23].C(N(CC)CC)C.[NH2:50][C:51]1[O:52][C:53]([C:56]2[O:57][CH:58]=[CH:59][CH:60]=2)=[N:54][N:55]=1>CN(C)C=O>[C:22]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[C:29]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH:28]=[C:27]2[C:40]([NH:50][C:51]1[O:52][C:53]([C:56]2[O:57][CH:58]=[CH:59][CH:60]=2)=[N:54][N:55]=1)=[O:41])#[N:23]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2021855-(Furan-2-yl)-1,3,4-oxadiazol-2-amineHCID 672048646-Cyano-2-phenyl-4-quinolinecarboxylic acid

Produkt 1

HCID 672054426-cyano-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinolinecarboxamideAusbeute 1,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HOBt (0.0351 g, 0.260 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (0.0460 g, 0.240 mmol) were added to a dimethylformamide (5.0 mL) solution of 6-cyano-2-phenyl-4-quinolinecarboxylic acid (0.0548 g, 0.200 mmol) described in Reference Example 22 and triethylamine (0.0223 g, 0.220 mmol), and the mixture was stirred at room temperature for 30 minutes. Commercially available 2-amino-5-(2-furyl)-1,3,4-oxadiazole (0.0332 g, 0.220 mmol) was added thereto, and the mixture was stirred at room temperature. The reaction solution was subjected to extraction with dichloromethane, washed with water and saturated saline, and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The obtained residue was fractionated by silica gel column chromatography, and the solvent was distilled off to obtain the title compound (0.001 g, 0.0024 mmol) as an amorphous substance.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature
  2. extractionThe reaction solution was subjected to extraction with dichloromethane
  3. washwashed with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-c97ce47cec8848cebce8b40a524003cc
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466290B2

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