HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 54670052, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Chloro-5-ethylpyrimidine | HCID 3572763 | — |
| Reactant | (S)-3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-one | HCID 66802663 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 54670052 | HCID 54670052 | 38.3% |
Reaction Steps
A stirred solution of (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-[1,4′-bipiperidin]-2-one (Preparation G; 18 mg, 0.047 mmol), DIEA (24 μL mL, 0.14 mmol), and 2-chloro-5-ethylpyrimidine (20 mg, 0.14 mmol) in DMF (1 mL) was heated at 100° C. for 2 hours in a sealed tube. The mixture was cooled, diluted with EtOAc (25 mL), washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative TLC (EtOAc/DCM 4:1) to afford (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1′-(5-ethylpyrimidin-2-yl)-[1,4′-bipiperidin]-2-one (9 mg, 0.018 mmol, 38% yield) as a white solid. Mass spectrum (apci) m/z=495.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08754226B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-cd508206a9954261abb346509d72b171 |
| Source note | uspto-grants-2014_06 |