Pentylamine → 5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]oxadiazole-2-carboxylic acid pentylamide

HRID 2074142

反応式

HRID 2074142 の反応式
C(O[C:4]([C:6]1[O:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:26])[F:25])[CH2:13][CH2:12]2)=[N:9][N:10]=1)=[O:5])C.[CH2:29]([NH2:34])[CH2:30][CH2:31][CH2:32][CH3:33].[C-]#N.[Na+]>>[CH2:29]([NH:34][C:4]([C:6]1[O:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:26])([F:27])[F:25])[CH2:13][CH2:12]2)=[N:9][N:10]=1)=[O:5])[CH2:30][CH2:31][CH2:32][CH3:33]

参加物

4

反応物 3

HCID 8060PentylamineHCID 8929Sodium CyanideHCID 57659021Ethyl 5-{4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl}-1,3,4-oxadiazole-2-carboxylate

生成物 1

HCID 115757855-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]oxadiazole-2-carboxylic acid pentylamide収率 86%

実験手順

5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-yl]-[1,3,4]oxadiazole-2-carboxylic acid ethyl ester (0.050 g, 0.126 mmol) was added to the mixture of n-pentylamine (1 mL) and sodium cyanide (0.012 g, 0.251 mmol). The reaction mixture was stirred at room temperature over night. The mixture was evaporated to dryness, then diluted with 5 mL of water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, and then concentrated. The title compound was obtained in 86% yield (0.047 g) after column purification. 1H NMR (300 MHz, CDCl3) δ 7.74-7.71 (m, 1H), 7.64-7.52 (m, 2H), 7.33-7.31 (m, 1H), 6.91 (t, J=5.4 Hz, 1H), 4.09-3.98 (m, 1H), 3.87-3.6 (m, 3H), 3.58-3.45 (m, 2H), 3.42-3.36 (m, 2H), 3.30-3.27 (m, 2H), 1.63-1.5 (m, 2H), 1.33-1.29 (m, 4H), 0.87 (t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.6, 164.6, 153.9, 153.5, 133.9, 132.4, 129.6, 128.97, 127.1, 126.9, 126.8, 126.7, 125.4, 121.8, 46.0, 45.7, 45.6, 40.8, 39.7, 29.0, 28.9, 22.3, 13.9. MS (ES+) m/z 440 (M+1).

後処理

  1. customThe mixture was evaporated to dryness
  2. additiondiluted with 5 mL of water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9ed67b452d084545b0e41b008fa8e0ad
出典データセット
uspto-grants-2011_04
特許番号
US07919496B2

関連ノート

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