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5-Hydroxyindoleacetic Acid → (S)-2-(5-hydroxy-1H-indol-3-yl)-N-(1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethyl)acetamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 5-Hydroxyindoleacetic Acid | HCID 1826 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| 反応物 | (S)-1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethanamine | HCID 90281302 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | (S)-2-(5-hydroxy-1H-indol-3-yl)-N-(1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethyl)acetamide | HCID 90281481 | — |
反応手順
(S)-1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethanamine (75 mg, 0.2 mmol), 2-(5-hydroxy-1H-indol-3-yl)acetic acid (47 mg, 0.25 mmol) and HATU (97 mg, 0.26 mmol) were combined in DMF (2 mL) and treated with diisopropylethylamine (70 μL). The reaction was stirred for 30 min and the purified by RP HPLC to provide the title compound: 1H NMR (400 MHz, DMSO-d6) δ 10.53 (d, 1H), 8.67 (d, 1H), 7.58 (s, 1H), 7.38-7.28 (m, 2H), 7.20-7.12 (m, 3H), 7.12-6.98 (m, 4H), 6.91-6.79 (m, 3H), 6.72 (d, 1H), 6.57 (dd, 1H), 5.38-5.31 (m, 1H), 5.17 (d, 2H), 3.71 (s, 3H), 3.40-3.22 (m, 3H), 3.16 (dd, 1H). MS (m/z) 481.2 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09220710B2 |
| 出典データセット | uspto-grants-2015_12 |
| ORD ID | ord-63d7455d3ed0433cbb7d4e53344b85e5 |
| 出典メモ | uspto-grants-2015_12 |