HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (z)-n-(2-Amino-4-chlorophenyl)-6-(2-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Sunitinib acid | HCID 10979489 | — |
| Reactant | N-(2-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamide | HCID 57993741 | — |
| Reactant | HCID 178418300 | HCID 178418300 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | (z)-n-(2-Amino-4-chlorophenyl)-6-(2-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide | HCID 44538558 | 76% |
Reaction Steps
5-(5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (300 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-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamide (321 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 (446 mg, 76%) as a yellow solid. LC-MS (m/z) 588 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158656B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-4e1d34f76f74478ab4f16b792466f8c8 |
| Source note | uspto-grants-2012_04 |