反応式
C(O/[CH:4]=[C:5]1\[C:6](=[O:24])[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[N:8]=[C:9]\1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1F)C.C(=O)([O-])[O-].[K+].[K+].[NH:31]1[C:39]2[C:34](=[CH:35][C:36]([CH2:40][NH2:41])=[CH:37][CH:38]=2)[CH:33]=[CH:32]1>O>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:7]1[C:6](=[O:24])[C:5]2=[CH:4][N:41]([CH2:40][C:36]3[CH:35]=[C:34]4[C:39](=[CH:38][CH:37]=3)[NH:31][CH:32]=[CH:33]4)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9]2=[N:8]1参加物
実験手順
(4Z)-4-[(Ethoxy)methylidene]-2,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one (236 mg, 0.720 mmol), potassium carbonate (100 mg, 0.720 mmol, 1 equiv) and 1-(1H-indol-5-yl)methanamine (105 mg, 0.720 mmol, 1 equiv) were combined and placed into a preheated oil bath at 100° C. open to the air for 2.5 hours. The mixture was cooled to ambient temperature, poured into water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 11.14 (1H, s), 9.12 (1H, s), 8.18 (1H, d, J=8.0 Hz), 7.89 (1H, d, J=9.0 Hz), 7.62-7.58 (2H, m), 7.53 (1H, s), 7.51 (1H, t, J=7.7 Hz), 7.48-7.38 (3H, m), 7.36-7.32 (2H, m), 7.09 (1H, d, J=8.6 Hz), 6.40 (1H, br m), 5.78 (2H, m) ppm; low resolution mass spectrometry (ES+) m/z 409.1449 [(M+H)+; calculated for C25H18FN4O: 409.1459].
後処理
- extractionextracted with ethyl acetate (3×100 mL)
- dry with materialThe combined organic extracts were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)
出典と根拠
- ORDレコード
- ord-f5b4535ca4024d399f92b3f048e150fd
- 出典データセット
- uspto-grants-2014_11
- 特許番号
- US08895580B2
関連ノート
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