Pyrrole-2-carboxaldehyde → 2-Oxo-3-(1h-pyrrol-2-ylmethylene)-2,3-dihydro-1h-indole-6-carboxylic acid (3-benzoylamino-phenyl)-amide
반응식
[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]=1참가 물질
실험 절차
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+).
후처리
- concentrationThe mixture is concentrated
출처 및 근거
- ORD 기록
- ord-50bffd2ee01841a18210610b8347474a
- 출처 데이터셋
- uspto-grants-2012_01
- 특허 번호
- US08101608B2
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