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Pyridine → N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Pyridine | HCID 1049 | — |
| 反応物 | Oxalyl chloride | HCID 65578 | — |
| 反応物 | 3-tert-Butylaniline | HCID 79334 | — |
| 反応物 | 1-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid | HCID 23282848 | — |
| 反応物 | tert-Butyl 4-(3-tert-butylphenylcarbamoyl)-4-methylpiperidine-1-carboxylate | HCID 86635224 | — |
| 触媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | 1,1-Dichloroethane | HCID 6365 | — |
| 生成物 | N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide | HCID 57920200 | 61% |
反応手順
Preparation of tert-Butyl 4-(3-tert-butylphenylcarbamoyl)-4-methylpiperidine-1-carboxylate. To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.30 g, 1.2 mmol), DMF (20 drops), and pyridine (0.38 g, 4.8 mmol) in dichloroethane (10 mL) was added oxalyl chloride (0.15 g, 1.2 mmol). The mixture was stirred for 40 minutes, and 3-tert-butylaniline was added. The mixture was stirred for 1 hour, diluted with dichloromethane, washed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl, dried over MgSO4, and concentrated. Silica gel chromatography (0-2% MeOH:CH2Cl2) gave the title compound in 61% yield. MS (ES+) [M+H]+375.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08450332B2 |
| 出典データセット | uspto-grants-2013_05 |
| ORD ID | ord-ed7a01bbd0af4d918e25666e97d4466e |
| 出典メモ | uspto-grants-2013_05 |