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].[CH3:33][CH2:34][CH2:35][C:36](Cl)=[O:37]>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](=[O:37])[CH2:35][CH2:34][CH3:33])[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 (0.8 g, 5.3 mmol) was added to a stirred suspension of 3-(4-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrochloride (0.7 g, 2.1 mmol) in acetonitrile (100 mL). The mixture was stirred for 30 minutes. n-Butyryl chloride (0.3 g, 3.2 mmol) was added, and the mixture was stirred at room temperature overnight. The mixture was concentrated, and the residue was stirred with CH2Cl2 (60 mL) and 2NHCl (30 mL). Solid was collected and slurried with ethanol (20 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-butyramide (0.5 g, 67%) as a white solid: mp 244-246° C.; 1H NMR (DMSO-d6) δ 0.85 (t, J=7.4 Hz, 3H, CH3), 1.40-1.60 (m, 2H), 1.99-2.14 (m, 3H), 2.34-2.65 (m, 2H), 2.86-2.98 (m, 1H), 4.32-4.53 (m, 4H), 5.11-5.18 (dd, J=4.9 and 13.2 Hz, 1H, CH), 7.48-7.64 (m, 3H, Ar), 8.13 (t, J=5.1 Hz, 1H, NH), 11.02 (s, 1H, NH); 13C NMR (DMSO-d6) δ 13.67; 18.65, 22.61, 31.19, 37.16, 38.93, 46.15, 51.54, 121.62, 128.29, 130.60, 131.63, 134.82, 140.08, 168.08, 171.02, 172.01, 172.88; Anal. calcd. for C18H21N3O4: C, 62.96; H, 6.16; N, 12.24. Found: C, 63.08; H, 6.06; N, 12.08.
後処理
- stirringthe mixture was stirred at room temperature overnight
- concentrationThe mixture was concentrated
- stirringthe residue was stirred with CH2Cl2 (60 mL) and 2NHCl (30 mL)
- customSolid was collected
出典と根拠
- ORDレコード
- ord-31feac5f26d14367b19f07aa86ebb4b3
- 出典データセット
- uspto-grants-2013_07
- 特許番号
- US08481568B2
関連ノート
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