HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → 3-cyclopropyl-3-[4-(5-methoxy-2-{[3-(1,3-oxazol-5-yl)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 3-(1,3-Oxazol-5-yl)aniline | HCID 2739289 | — |
| Reactant | 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile | HCID 86637303 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-cyclopropyl-3-[4-(5-methoxy-2-{[3-(1,3-oxazol-5-yl)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile | HCID 58014655 | — |
Reaction Steps
A mixture of 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile (20 mg, 0.00008 mol), 3-(1,3-oxazol-5-yl)aniline (18.1 mg, 0.000113 mol), and p-toluenesulfonic acid (11 mg, 0.000064 mol) in dry 1,4-dioxane (0.5 mL, 0.006 mol) was refluxed overnight. The mixture was diluted with acetonitrile and water, purified on RP-HPLC at pH 10 to give the desired product as a racemic mixture (free base). LCMS (M+H) 428.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309718B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-d686a13dad3b47e5a07e4e5f506cf4c4 |
| Source note | uspto-grants-2012_11 |