HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Amino-3-phenylisoxazole → (R)-2-(4-cyano-2-fluoro-5-(3-phenylisoxazol-5-ylamino)phenylamino)-3-cyclopropylpropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Amino-3-phenylisoxazole | HCID 261201 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium Phenoxide Trihydrate | HCID 23681143 | — |
| Reactant | (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-cyclopropylpropanamide | HCID 67508107 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-2-(4-cyano-2-fluoro-5-(3-phenylisoxazol-5-ylamino)phenylamino)-3-cyclopropylpropanamide | HCID 67508272 | 40.2% |
Reaction Steps
A mixture of (R)-2-(5-bromo-4-cyano-2-fluorophenylamino)-3-cyclopropylpropanamide (150 mg, 0.460 mmol), 5-amino-3-phenylisoxazole (100 mg, 0.625 mmol), sodium phenoxide trihydrate (100 mg, 0.588 mmol), xantphos (60 mg, 0.103 mmol) and Pd2 dba3 (40 mg, 0.043 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 120 C for 18 h. HOAc (0.5 mL) was added. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(4-cyano-2-fluoro-5-(3-phenylisoxazol-5-ylamino)phenylamino)-3-cyclopropylpropanamide (75 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846928B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-ae42da722a9149628ed012dc8ab94ba8 |
| Source note | uspto-grants-2014_09 |