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Diisopropylethylamine → 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | 2-(Thiazolo[5,4-b]pyridin-2-yl)aniline | HCID 58101468 | — |
| 反応物 | 5-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid | HCID 58551908 | — |
| 反応物 | 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium | HCID 86621144 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide | HCID 58551901 | 66% |
反応手順
2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (669 mg, 1.8 mmol) was added to a solution of 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (504 mg, 1.7 mmol), DIPEA (613 μL, 3.5 mmol), and 2-(thiazolo[5,4-b]pyridin-2-yl)aniline b (250 mg, 1.1 mmol) in DMF (7 mL). The reaction mixture was stirred for 16 h, poured into sat aq NaHCO3 and extracted with EtOAc. The organic fractions were washed with brine, dried and concentrated. The crude product was crystallized from EtOH to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (372 mg, 66% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08492401B2 |
| 出典データセット | uspto-grants-2013_07 |
| ORD ID | ord-d34b1801a0b94ee3a4538788698033ce |
| 出典メモ | uspto-grants-2013_07 |