反応式
[C:1]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[CH:27]=[C:26]3[C:22]([CH2:23][C:24](=[O:28])[NH:25]3)=[CH:21][CH:20]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH:34]=O>C(O)C.N1CCCCC1>[C:1]([NH:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([C:19]2[CH:27]=[C:26]3[C:22]([C:23](=[CH:34][C:30]4[NH:29][CH:33]=[CH:32][CH:31]=4)[C:24](=[O:28])[NH:25]3)=[CH:21][CH:20]=2)=[O:18])[CH:13]=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1参加物
実験手順
To a solution of 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid (0.20 g, 1.1 mmol) in DMF (1 ml) is added N-(3-amino-phenyl)-benzamide (0.26 g, 1.2 mmol), N,N-diisopropylethylamine (0.44 g, 3.4 mmol) and HATU (0.47 g, 1.24 mmol). The reaction is stirred for 20 hours and concentrated. The residue is purified by HPLC (C18 column, eluted with CH3CN—H2O containing 0.05% TFA) to give 2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid (3-benzoylamino-phenyl)-amide as off-white solid. This amide (15 mg, 0.04 mmol) is then heated with 1H-pyrrole-2-carbaldehyde (6.0 mg, 0.06 mmol) in ethanol (2 ml) in the presence of 2 drops of piperidine at 80° C. for 20 hours. The mixture is concentrated and the desired compound is obtained after HPLC purification: 1H NMR (DMSO-d6) δ 6.41 (s, 1H), 6.93 (s, 1H), 7.31 (t, 1H, J=7.8 Hz), 7.44 (s, 1H), 7.48-7.51 (m, 3H), 7.54 (t, 2H, J=7.2 Hz), 7.59 (d, 1H, J=6.6 Hz), 7.70 (d, 1H, J=8.4 Hz), 7.78 (d, 1H, J=8.4 Hz), 7.92 (s, 1H), 7.98 (d, 2H, J=7.2 Hz), 8.33 (s, 1H), 10.27 (s, 1H), 10.31 (s, 1H), 11.13 (s, 1H), 13.38 (s, 1H); LC-MS: 449.1 (MH+).
後処理
- concentrationThe mixture is concentrated
出典と根拠
- ORDレコード
- ord-50bffd2ee01841a18210610b8347474a
- 出典データセット
- uspto-grants-2012_01
- 特許番号
- US08101608B2
関連ノート
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