HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Tartaric acid → HCID 86658827, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Tartaric acid | HCID 444305 | — |
| Reactant | 5-fluoro-1,3-dihydro-2H-indol-2-one | HCID 3731012 | — |
| Reactant | N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide | HCID 20761785 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Pyrrolidine | HCID 31268 | — |
| Product | HCID 86658827 | HCID 86658827 | 61.5% |
Reaction Steps
To a solution of 6.63 g (25 mmol) N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (I) and 3.78 g (25 mmol) 5-fluoroindolin-2-one (II) in ethanol (400 ml), 0.25 ml of pyrrolidine was added and mixture was refluxed for 5 h. To a boiling reaction mixture, a solution of L-tartaric acid (1.88 g, 12.5 mmol) in ethanol (20 ml) was added and a solution was left to cool to room temperature, with slow (as slow as possible) stirring. The stirring was continued for another 16 hours, then the product was filtered to get 4.20 g of sunitinib L-tartarate. Melting point: 219-223° C. (Form III), ratio sunitinib/tartaric acid (according to NMR) 2:1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08686023B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-05901a29b5d74be6990103927b487394 |
| Source note | uspto-grants-2014_04 |