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

HRID 1259853

반응식

HRID 1259853 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c97ce47cec8848cebce8b40a524003cc
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466290B2

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