HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 6-(((dimethylamino)ethyl)amino)-3-(pivaloyloxy)-7H-indeno[2,1-c]quinoline-7-on
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pivaloyl chloride | HCID 62493 | — |
| Reactant | TAS-103 free base | HCID 135413533 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-(((dimethylamino)ethyl)amino)-3-(pivaloyloxy)-7H-indeno[2,1-c]quinoline-7-on | HCID 22371660 | 83.8% |
Reaction Steps
To a solution of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol) in dichloromethane (10 ml) was added 4-dimethylaminopyridine (100 mg, 0.8 mmol) and pivaloyl chloride (37 μl, 0.3 mmol), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added water to wash the organic layer, which was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (eluent; chloroform:ethanol=10:1(v/v)) and crystallized from hexane to give 105 mg (yield: 80.0%) of title compound. The physicochemical properties thereof are shown in table 1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06028079 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-9f4780708aff4fbfa89d6a993c861ecd |
| Source note | uspto-grants-2000_02 |