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Chloroacetyl chloride → propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Chloroacetyl chloride | HCID 6577 | — |
| 反応物 | Piperidine | HCID 8082 | — |
| 反応物 | Cyclohexanemethylamine | HCID 76688 | — |
| 反応物 | Diisopropyl malonate | HCID 83223 | — |
| 反応物 | 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde | HCID 5372812 | — |
| 反応物 | Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate | HCID 51050080 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 生成物 | propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate | HCID 178459409 | 20% |
反応手順
A solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.44 mmol) which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, and aminomethylcyclohexane (0.063 mL, 0.48 mmol) in 2-propanol (2.0 mL) was stirred at ambient temperature for 14 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) and piperidine (0.0044 mL, 0.044 mmol) were added then the mixture was refluxed for further 8 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.036 g, y. 19%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08742113B2 |
| 出典データセット | uspto-grants-2014_06 |
| ORD ID | ord-20dde74e66a94bd095fda331e0a36e7d |
| 出典メモ | uspto-grants-2014_06 |