HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Pyridine → N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Pyridine | HCID 1049 | — |
| Edukt | Oxalyl chloride | HCID 65578 | — |
| Edukt | 3-tert-Butylaniline | HCID 79334 | — |
| Edukt | 1-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid | HCID 23282848 | — |
| Edukt | HCID 86635224 | HCID 86635224 | — |
| Katalysator | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | 1,1-Dichloroethane | HCID 6365 | — |
| Produkt | N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide | HCID 57920200 | 61% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08450332B2 |
| Quelldatensatz | uspto-grants-2013_05 |
| ORD ID | ord-ed7a01bbd0af4d918e25666e97d4466e |
| Quellennotiz | uspto-grants-2013_05 |