Diethylamine → 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide

HRID 1372396ノート

反応式

HRID 1372396 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([OH:15])=O)[C:5]=2[C:4](=[O:16])[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCl>[CH3:17][C:2]1([CH3:1])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])=[O:15])[C:5]=2[C:4](=[O:16])[CH2:3]1

参加物

5

反応物 3

HCID 8021DiethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

生成物 1

HCID 225710523-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethylpropionamide収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 1.18 g of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (5 mmol) in dichloromethane (25 mL) was added 0.97 g (6 mmol) of carbonyldiimidazole. After stirring at room temperature for 2 hours, 2.1 mL (20 mmol) of diethylamine was added. The mixture was stirred at room temperature overnight. The reaction was concentrated and the residue dissolved in dichloromethane, washed with brine, dried and concentrated to give 1.2 g (83% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-diethyl-propionamide as a white solid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 10.91 (br s, 1H, NH), 6.46 (s, 1H), 3.20–3.29 (m, 4H, 2×CH2), 2.72–2.76 (m, 2H, CH2), 2.57 (s, 2H, CH2), 2.45 (m, 2H, CH2), 2.17 (s, 2H, CH2), 0.96–1.06 (m, 12H, 4×CH3). MS m/z 290 [M+].

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationThe reaction was concentrated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-793e3c418f9a4706bd9ef5e0e390f21c
出典データセット
uspto-grants-2007_01
特許番号
US07157577B2

反応ノート

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