Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | m-Toluidine | HCID 7934 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide | HCID 86685528 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Catalyst | Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene | HCID 129828017 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86685605 | HCID 86685605 | — |
Reaction Steps
To a mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-4-methylpentanamide (75 mg, 0.28 mmol) in toluene (1.5 mL) and dioxane (0.5 mL) was added m-toluidine (45 mg, 0.42 mmol), Pd(dba)2 (16 mg, 0.028 mmoL), Q-Phos (30 mg, 0.042 mmol) and Cs2CO3 (274 mg, 0.84 mmol). After heating at 95° C. for 15 h, the mixture was filtered, the filtrate was concentrated and purified by column chromatography to give (R)-2-(5-cyano-6-(m-tolylamino)pyrazin-2-ylamino)-4-methylpentanamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08877760B2 |
|---|
| Source dataset | uspto-grants-2014_11 |
|---|
| ORD ID | ord-1a26a96ff3214976aaa21e02b85e0ea3 |
|---|
| Source note | uspto-grants-2014_11 |
|---|
