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

HRID 1259853

Reaction equation

HRID 1259853 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 672054426-cyano-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinolinecarboxamideYield 1.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c97ce47cec8848cebce8b40a524003cc
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Linked notes

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