HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine-2-carbonitrile → 6-Phenyl-7-(4-{[4-(3-pyridin-2-yl-1,2,4-triazol-5-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine-2-carbonitrile | HCID 7522 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate | HCID 22713165 | — |
| Reactant | 4-(6-Phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde | HCID 86630655 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 6-Phenyl-7-(4-{[4-(3-pyridin-2-yl-1,2,4-triazol-5-yl)piperidin-1-yl]methyl}phenyl)imidazo[1,2-a]pyrimidine | HCID 25189685 | — |
Reaction Steps
0.55 ml triethylamine is added to a solution of 0.5 g 4-(6-phenylimidazo[1,2-a]pyrimidin-7-yl)benzaldehyde in 15 ml methanol. To this solution a solution of 0.6 g 2-(5-Piperidin-[1,2,4]triazol-3-yl)-pyridine*2HCl (prepared from tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate and pyridine-2-carbonitrile according to a procedure described in U.S. Pat. No. 4,011,218 or WO2005100344) in 15 ml DMF is added, followed by 0.25 ml glacial acetic acid and 700 mg NaBH(OAc)3. The resulting mixture is stirred at room temperature. Three additional portions of 2 equivalents NaBH(OAc)3 are added after 2, 4 and 20 hours.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08614218B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-3c26c67be31a458a81406284b907b508 |
| Source note | uspto-grants-2013_12 |