HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → n-(2-Aminophenyl)-6-(6-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)hexylamino)nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-(2-aminophenyl)-6-(6-aminohexylamino)nicotinamide | HCID 57993736 | — |
| Reactant | 2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid | HCID 137252512 | — |
| Reactant | HCID 178418300 | HCID 178418300 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | n-(2-Aminophenyl)-6-(6-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)hexylamino)nicotinamide | HCID 136647729 | 67% |
Reaction Steps
2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (328 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-aminophenyl)-6-(6-aminohexylamino)nicotinamide (343 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (427 mg, 67%) as a red solid. LC-MS (m/z) 638 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158656B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-3e373a6cd0f74f64807d35bfa45ecfbc |
| Source note | uspto-grants-2012_04 |