HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → 3-cyclopropyl-3-(4-{5-methoxy-2-[(3-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 3-Nitroaniline | HCID 7423 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| 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-nitrophenyl)amino]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile | HCID 58014501 | — |
Reaction Steps
A solution of a mixture of 3-[4-(2-chloro-5-methoxypyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopropylpropanenitrile (from example 320 step 1, 60 mg, 0.0002 mol), m-nitroaniline (40.9 mg, 0.000296 mol), and p-toluenesulfonic acid (29 mg, 0.00017 mol) in dry 1,4-dioxane (1 mL, 0.02 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) 406.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309718B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-0f6384c5713d47f5968c53ac63982cba |
| Source note | uspto-grants-2012_11 |