HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 3-cyclopentyl-3-[4-(2-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline | HCID 6493749 | — |
| Reactant | 3-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile | HCID 86637288 | — |
| Product | 3-cyclopentyl-3-[4-(2-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile | HCID 58014513 | — |
Reaction Steps
A mixture of 3-[4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl]-3-cyclopentylpropanenitrile (prepared according to the procedure described in Example 33, Step 2; 0.030 g, 0.000099 mol) and 4-(2-pyrrolidin-1-ylethoxy)aniline (0.0308 g, 0.000149 mol) in acetic acid (0.7 mL, 0.01 mol) was refluxed overnight. After being evaporated to dryness, the residue was diluted with EtOAc, washed with aqueous sodium bicarbonate, brine, dried, and concentrated. The residue was applied on RP-HPLC to obtain the desired product as a racemic mixture (free base). LCMS (M+H) 472.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309718B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-6a8c111bd6fe4680b1f74623ef0e296a |
| Source note | uspto-grants-2012_11 |