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Dimethylformamide → 2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 3-Bromopyridine-2-carboxylic Acid | HCID 2050129 | — |
| 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 | 5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine | HCID 13247046 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 2-bromo-6-{[(3R)-3-methoxypyrrolidin-1-yl]carbonyl}pyridine | HCID 59525609 | — |
反応手順
A solution of HOBt (148 mg, 0.97 mmol), DIEA (130 μL, 0.74 mmol), HATU (367 mg, 0.97 mmol), bromopyridine-2-carboxylic acid (150 mg, 0.74 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (91 mg, 0.74 mmol) in DMF (2.5 mL) was stirred overnight at 65° C. Upon completion, Si-carbonate (2.8 g, 2.23 mmol) and DCM (3 mL) were added and the mixture was shaken overnight at room temperature. The resulting mixture was then filtered, washed with DCM, concentrated in vacuo and purified by reverse phase HPLC (acetonitrile/water+formic acid modifier) to afford the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08367706B2 |
| 出典データセット | uspto-grants-2013_02 |
| ORD ID | ord-ef6d136ec9034e4880c918885b1dd270 |
| 出典メモ | uspto-grants-2013_02 |