Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Reactant | HCID 67327163 | HCID 67327163 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 53358060 | HCID 53358060 | 71% |
Reaction Steps
6-Chloronicotinonitrile (0.04 g, 0.29 mmol) and triethylamine (0.15 mL, 1.08 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 0.11 g, 0.24 mmol) in dichloromethane (3.3 mL) and the resulting mixture was stirred at 50° C. for 20 hours. The reaction mixture was then cooled to ambient temperature and dichloromethane and 4% aqueous sodium hydrogencarbonate solution were added. The organic layer was separated, washed with water and brine, dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography (200:1 to 60:1 chloroform/methanol) to give the title compound (0.07 g, 71%) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206183B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-ae21d8d747f84bdfb822994bcb910138 |
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| Source note | uspto-grants-2015_12 |
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