HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Methyl 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Cyclobutyl-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)urea | HCID 66661134 | — |
| Reactant | Methyl 2-(methylsulfonylmethyl)isonicotinate | HCID 66661272 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Methyl 2-((4-(4-(3-cyclobutylureido)-3-fluorobenzoyl)piperazin-1-yl)methyl)isonicotinate | HCID 66661722 | 58.6% |
Reaction Steps
Methyl 2-(methylsulfonylmethyl)isonicotinate (2.99 mmol, 0.686 g), 1-cyclobutyl-3-(2-fluoro-4-(piperazine-1-carbonyl)phenyl)urea (2.99 mmol, 0.959 g) and potassium carbonate (8.98 mmol, 1.241 g) were combined and heated to 40° C. in acetonitrile (20 mL) for 2 hours. The reaction mixture was concentrated at reduced pressure and the residue taken up in dichloromethane. The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 6% methanol/dichloromethane) to afford the title compound (822 mg). MS (ESI) m/z 470.5 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759352B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-6f380e94ded24c6a87398a29c959534b |
| Source note | uspto-grants-2014_06 |