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Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 5-Chloro-1H-indole-3-ethylamine monohydrochloride | HCID 2827494 | — |
| 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 | Ethyl 5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate | HCID 63379544 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Sodium Hydroxide | HCID 14798 | — |
| 生成物 | N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxamide | HCID 66832051 | 21% |
反応手順
This compound was prepared according to method F with ethyl 5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate (0.115 g; 0.433 mmol) in THF (1 mL) and sodium hydroxide in water (2M, 1 mL); and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.433 mmol), HATU (0.164 g; 0.432 mmol), N,N diisopropylethylamine (0.075 mL; 0.432 mmol), in DMF (4 mL). The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and preparative HPLC method 2 to yield 0.0377 g (21%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(3-chlorobenzyl)-1,2,4-oxadiazole-3-carboxamide as a white solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09434722B2 |
| 出典データセット | uspto-grants-2016_09 |
| ORD ID | ord-249935c22ee040e691516b5069c2d5d9 |
| 出典メモ | uspto-grants-2016_09 |