化工社化工社 化学情報印刷レポート · 研究参考用
Ammonium Hydroxide → 5-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ammonium Hydroxide | HCID 14923 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 4-Methylsulfonylbenzylamine hydrochloride | HCID 2729269 | — |
| 反応物 | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| 反応物 | 5-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid | HCID 86711528 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 5-Bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide | HCID 86711536 | — |
反応手順
A solution of 5-bromo-1-(4-cyano-benzyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 1c, 1.00 g, 2.88 mmol), TBTU (0.925 g, 2.88 mmol), DIPEA (1.50 mL, 8.67 mmol) in DMF (7 mL) is stirred for 30 min. Then, 4-(methylsulfonyl)benzylamine hydrochloride (0.766 g, 3.46 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with MeOH, basified with NH4OH, filtered and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 0.66 g (29% of theory); ESI mass spectrum: [M+H]+=514 (bromine isotope pattern); Retention time HPLC: 0.88 min (Z003—001).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09102624B2 |
| 出典データセット | uspto-grants-2015_08 |
| ORD ID | ord-c0794c0ca32f45fcba4356828349a91d |
| 出典メモ | uspto-grants-2015_08 |