Dimethylformamide → HCID 16730933、化合物

HRID 226950

反応式

HRID 226950 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2C(=[CH:13][CH:14]=[CH:15][CH:16]=2)NC=1)=[O:8].Cl[CH2:25][C:26]1N=[CH:29][O:28][N:27]=1.[C:31](#N)C.[CH3:34][N:35]([CH3:38])[CH:36]=O>>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:34](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:35]([CH2:38][C:26]2[CH:25]=[C:29]([CH3:31])[O:28][N:27]=2)[CH:36]=1)=[O:8]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

生成物 1

HCID 16730933HCID 16730933、化合物

反応条件

温度
80 °C

実験手順

26 mg (0.65 mmol) of sodium hydride (60%) was suspended in 3 mL of anhydrous dimethylformamide and to it was added 138.7 mg (0.50 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a and the resultant mixture was stirred at rt for 30 min. Then 77.4 mg (0.65 mmol) of 3-chloromethyl-1,2,4-oxadiazole was added to the reaction solution and the mixture was stirred at 80° C. for 1 h. The reaction solution was quenched by the addition of 10 mL of water. The crude product precipitated out of solution and was isolated by filtration. Purification of the crude product by flash chromatography provided 55 mg of 4cc as a colorless solid: LC-MSD, m/z for C23H20N2O3, [M+H]+=373.4, [M+2H]+=374.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time =2.639 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.30 (d, 6H), 2.36 (s, 3H), 5.38 (s, 2H), 5.90 (s, 1H), 7.15 (d, 1H), 7.42 (t, 1H), 7.50-7.68 (m, 4H), 8.27 (s, 1H), 8.44 (d, 1H).

後処理

  1. customThe reaction solution was quenched by the addition of 10 mL of water
  2. customThe crude product precipitated out of solution
  3. customwas isolated by filtration
  4. customPurification of the crude product by flash chromatography
  5. customprovided 55 mg of 4cc as a colorless solid

出典と根拠

ORDレコード
ord-b1b7d3dc6c0d410b90c1fceaad4c1d8e
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

関連ノート

読み込み中…