HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 1-(6-amino-3'-fluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-2'-yl)azetidin-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Hydroxyazetidine hydrochloride | HCID 2759290 | — |
| Reactant | 2',3'-difluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-6-amine | HCID 67466925 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 1-(6-amino-3'-fluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-2'-yl)azetidin-3-ol | HCID 54588543 | 30% |
Reaction Steps
2′,3′-Difluoro-5-[(R)-1-(5-fluoro-2-[1,2,3]triazol-2-yl-phenyl)-ethoxy-[3,4′]bipyridinyl-6-ylamine (example 129) (35 mg, 0.085 mmol, 1.0 eq) and potassium carbonate (115 mg, 0.833 mmol, 9.8 eq) and 3-hydroxyazetidine hydrochloride (91.3 mg, 0.833 mmol, 9.8 eq) in anhydrous DMSO (2 mL) were microwaved for 10 min. at 150° C. The mixture was filtered, concentrated, and purified with a reverse phase pre-HPLC under acidic condition to give the title compound (11.8 mg, 30% yield) as a amorphous solid after lyophilization.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08916593B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-97ad367bd4c4492ea651ceb533b61456 |
| Source note | uspto-grants-2014_12 |