Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | ethyl 3-chloro-2,4-dioxopentanoate | HCID 3006755 | — |
| Reactant | HCID 178418806 | HCID 178418806 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 69005522 | HCID 69005522 | 20% |
Reaction Steps
3-Chloro-2,4-dioxo-pentanoic ethyl ester (0.325 g, 1.685 mmol) is added to a solution of 3-aminopyrazole (0.14 g, 1.685 mmol) and piperidine (0.18 mL, 1.85 mmol) in MeCN (15 mL), and the reaction mixture heated at 90° C. for 17 hours. After cooling to room temperature, the reaction mixture is diluted with EtOH and concentrated. Purification by flash chromatography (0.5% MeOH in methylene chloride) gives 80 mg (20%) desired product. 1H NMR (400 mHz, CD3OD) δ 8.27 (d, 1H), 6.84 (d, 1H), 4.48 (q, 2H), 2.97 (s, 3H), 1.42 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07576072B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-c386aaae964f4a1795f2ba01eef0487c |
|---|
| Source note | uspto-grants-2009_08 |
|---|