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Phosphorus tribromide → US9433622, Dmx-156
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Phosphorus tribromide | HCID 24614 | — |
| 反応物 | Piperazin-2-one | HCID 231360 | — |
| 反応物 | 3-((S)-3-Fluoro-pyrrolidin-1-yl)-6-[2-(6-hydroxymethyl-pyridin-3-ylamino)-pyrimidin-4-yl]-pyridine-2-carbonitrile | HCID 90369544 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | US9433622, Dmx-156 | HCID 90356780 | 6.3% |
反応手順
Compound 82 (40 mg, 0.10 mmol) was dissolved in MeCN (5 mL). Phosphorous tribromide (50 μL, 0.53 mmol) was added and the reaction mixture was heated under reflux for 0.5 hours. The reaction was cooled to rt and 2-oxopiperazine (100 mg, 0.99 mmol) was added and the reaction mixture stirred at rt for 16 hours. The solvent was removed in vacuo and the residue purified by reverse phase preparative LC-MS. Fractions contained the desired product were combined and the MeOH removed in vacuo. The resulting aqueous solution was frozen (−78° C.) and the solvent evaporated in vacuo (freeze dried). The title compound (3 mg, 6%) was obtained as an off-white solid. LCMS, Rt=6.15 min (MeOH-FA method), m/z 474 (MH+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09433622B2 |
| 出典データセット | uspto-grants-2016_09 |
| ORD ID | ord-56f9dfa100104078a8c79c39ac5578f0 |
| 出典メモ | uspto-grants-2016_09 |