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N-Methylphenylethanolamine → N-(4-chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | N-Methylphenylethanolamine | HCID 913 | — |
| 反応物 | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| 反応物 | Methanesulfonyl chloride | HCID 31297 | — |
| 反応物 | N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide | HCID 6482399 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | N-(4-chlorobenzyl)-2-(((2-hydroxy-2-phenylethyl)(methyl)amino)methyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide | HCID 10458488 | 63.6% |
反応手順
To a solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (17 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 1 h and then α-(methylaminomethyl)benzyl alcohol (1.26 g) is added. The mixture is stirred at room temperature for 18 h and is then poured into water (50 mL). The resulting off-white solid is filtered off and purified by column chromatography (CH2Cl2/methanol, 99/1; 97/3) to yield 0.261 g (63%) of the title compound as a pale yellow solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06239142B1 |
| 出典データセット | uspto-grants-2001_05 |
| ORD ID | ord-9b7cc8f6848444c88a1ae3b3c78c4462 |
| 出典メモ | uspto-grants-2001_05 |