反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:25]([O:27][C:28](=[O:32])[CH2:29][CH2:30]Cl)[CH3:26]>CN(C=O)C>[CH2:25]([O:27][C:28](=[O:32])[CH2:29][CH2:30][N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[N:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH3:26]参加物
実験手順
To a solution of 2-[3-(1H-indol-5-yl)-propyl]-[1,8]naphthyridine (0.180 g, 0.627 mmol) in DMF (2 mL) was added sodium hydride (24.0 mg. 1.00 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 h. After cooling to 0° C., 3-chloro-propionic acid ethyl ester (85.0 mg, 0.63 mmol) was added and stirred overnight at room temperature. Ice water was added and the resulting mixture was extracted with methylene chloride. The combined organic layers were washed with water and brine, and dried over Na2SO4. Chromatography of the crude product on silica gel (methylene chloride/methanol, 95:5) gave the title product (0.11 g, 45% yield). 1H NMR (CDCl3) δ 9.08 (d, 1H), 8.13 (d, 1H), 8.08 (d, 1H), 7.30-7.50 (m, 4H), 7.10 (m, 2M), 6.40 (dd, 1H), 4.40 (t, 2H), 4.10 (m, 2H), 3.10 (t, 2H), 2.80 (m, 4H), 2.25 (m, 2H), 1.20 (q, 3H).
後処理
- temperatureAfter cooling to 0° C.
- stirringstirred overnight at room temperature
- extractionthe resulting mixture was extracted with methylene chloride
- washThe combined organic layers were washed with water and brine
- dry with materialdried over Na2SO4
出典と根拠
- ORDレコード
- ord-069d4e666c8b4f96bd4b7e184da8a28f
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06855722B2
関連ノート
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