HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(3-pyridinyl)-1H-imidazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 3-Aminopyridine | HCID 10009 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid | HCID 21868804 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(3-pyridinyl)-1H-imidazole-4-carboxamide | HCID 22285436 | 54.2% |
Reaction Steps
2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid (403 mg, 1.2 mmol) was dissolved in dichloromethane (5 mL) and treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (459 mg, 1.56 mmol) and N-methylmorpholine (NMM) (182 mg, 1.8 mmol). The mixture was stirred under argon for 15 minutes before 3-aminopyridine (349 mg, 3.6 mmol) was added. Stirring at rt was continued overnight. The reaction mixture was then adsorbed onto silica gel and chromatographed (2-3% MeOH in CH2Cl2) to afford 2-(2-chlorophenyl)-1-(4-chlorophenyl)-N-(3-pyridinyl)-1H-imidazole-4-carboxamide (266 mg, 54% yield): LC-MS m/z 409.3, retention time 2.43 min (method 1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06960601B2 |
| Source dataset | uspto-grants-2005_11 |
| ORD ID | ord-2a69460dcde14ec69cc7a1a7f6e641d4 |
| Source note | uspto-grants-2005_11 |