HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (R)-2-(5-cyano-6-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)pyrazin-2-ylamino)butanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 6-amino-3,4-dihydroquinolin-2(1H)-one | HCID 4912759 | — |
| Reactant | (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide | HCID 86685581 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-2-(5-cyano-6-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)pyrazin-2-ylamino)butanamide | HCID 86685586 | 59% |
Reaction Steps
A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)butanamide (80 mg, 0.334 mmol), 6-amino-3,4-dihydroquinolin-2(1H)-one (60 mg, 0.370 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (25 mg, 0.040 mmol) and Pd(OAc)2 (10 mg, 0.044 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 4 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)pyrazin-2-ylamino)butanamide (72 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08877760B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-77271ab94614443fb5becbfe526e2306 |
| Source note | uspto-grants-2014_11 |