反応式
N12CCCN=C1CCCCC2.Cl.[NH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][N:18]([CH:25]1[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:19]2=[O:24].[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34]>C(#N)C>[O:32]=[C:26]1[CH:25]([N:18]2[CH2:17][C:16]3[C:20](=[CH:21][CH:22]=[CH:23][C:15]=3[CH2:14][NH:13][C:36]([NH:35][CH2:33][CH3:34])=[O:37])[C:19]2=[O:24])[CH2:30][CH2:29][C:28](=[O:31])[NH:27]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
1,8-Diazabicyclo[5,4,0]undec-7-ene (0.44 g, 2.91 mmol) was added to a stirred suspension of 3-[4-(aminomethyl)-1-oxoisoindolin-2-yl]piperidine-2,6-dione hydrochloride (0.6 g, 1.94 mmol) in acetonitrile (50 mL). After stirring for 30 min, ethyl isocyanate (0.21 g, 2.91 mmol) was added. The mixture was stirred at room temperature for 17 hours. Solvent was removed and the residue was stirred with methylene chloride (70 mL) to give N-{[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]methyl}(ethylamino)carboxamide (0.28 g, 42%) as a white solid: mp 341–343° C.; 1H NMR (DMSO-d6) δ 11.02 (s, 1H), 7.62–7.47 (m, 3H), 6.40 (t, J=5.9 Hz, 1H), 5.95 (t, J=5.6 Hz, 1H), 5.18–5.10 (dd, J=5.3 and 13.3 Hz, 1H), 4.52–4.30 (dd, J=17.3 and 37.7 Hz, 2H), 4.28 (d, J=5.9 Hz, 2H), 3.04 (q, J=7.2 Hz, 2H), 3.01–2.86 (m, 1H), 2.65–2.34 (m, 2H0, 2.04–1.99 (m, 1H), 0.98 (t, J=7.2 Ha, 3H); 13C NMR (DMSO-6) δ 172.82, 170.97, 168.10, 157.86, 139.78, 136.24, 131.55, 130.25, 128.16, 121.32, 51.51, 46.13, 34.14, 31.16, 22.59, 15.67; Anal. Calcd for C17H20N4O4: C, 59.29; H, 5.85; N, 16.27. Found: C, 58.98; H, 5.85; N, 16.89.
後処理
- stirringThe mixture was stirred at room temperature for 17 hours
- customSolvent was removed
- stirringthe residue was stirred with methylene chloride (70 mL)
出典と根拠
- ORDレコード
- ord-265838542203460ba52244619f8d3caf
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07091353B2
関連ノート
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