HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 3-amino-N-cyclopropyl-4-methylbenzamide | HCID 11983854 | — |
| Reactant | 1-(2,6-Dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid | HCID 65501190 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide | HCID 59234669 | 66.7% |
Reaction Steps
To a solution of 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (56 mg) in DMF (0.76 mL) were added 3-amino-N-cyclopropyl-4-methylbenzamide (45 mg), WSC—HCl (57 mg), HOBt (35 mg) and Et3N (27 mg), and the mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was diluted with EtOAc (2 mL), washed with water (4 mL×2) and brine successively, dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by preparative thin layer chromatography eluting with 10% MeOH in CH2Cl2 to give N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide (60 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173684B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-4cc668a498dc477185fafd0183ef0af1 |
| Source note | uspto-grants-2012_05 |