HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Aminoquinoline → (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Aminoquinoline | HCID 11375 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)propanamide | HCID 86685533 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamide | HCID 86685535 | 51.6% |
Reaction Steps
A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)propanamide (97 mg, 0.430 mmol), 3-aminoquinoline (62 mg, 0.430 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(quinolin-3-ylamino)pyrazin-2-ylamino)propanamide (74 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359308B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-55706e70293a4970aac780e338337a7b |
| Source note | uspto-grants-2016_06 |