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

HRID 1259853

反応式

HRID 1259853 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c97ce47cec8848cebce8b40a524003cc
出典データセット
uspto-grants-2013_06
特許番号
US08466290B2

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