HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Dimethylaminopyridine → N-Propanesulphonyl-6-[N-(5-bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Propane-1-sulphonamide | HCID 3401849 | — |
| Reactant | 6-[N-(5-Bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic acid | HCID 10135994 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Solvent | Dichloromethane ethanol | HCID 21584144 | — |
| Product | N-Propanesulphonyl-6-[N-(5-bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide | HCID 18693268 | — |
Reaction Steps
6-[N-(5-Bromo-2-(2-methylprop-2-enyloxy)benzyl)-N-ethylamino]pyridazin-3-carboxylic acid (185 mg, 0.46 mmol) was dissolved in dichloromethane (20 ml), (1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDAC), dimethylaminopyridine, (DMAP) (111 mg, 0.91 mmol) and propanesulfonamide (68 mg, 0.55 mmol) were added. The mixture was stirred at ambient temperature under argon overnight, after which TLC (25% water/CH3CN) suggested the reaction was complete. The reaction mixture was loaded directly onto a MPLC column (silica) and the title compound obtained by elution with 5% EtOH/CH2Cl2 then 5% EtOH/0.5% AcOH/CH2Cl2, as a clear oil which solidified on triturating with hexane to give a colourless powder (110 mg, 47%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06100258 |
| Source dataset | uspto-grants-2000_08 |
| ORD ID | ord-b9cf3959f96f4e03b2eb657f0673b830 |
| Source note | uspto-grants-2000_08 |