HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}cyclopropanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | 1-[(1R,2R)-2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine dihydrochloride | HCID 66720635 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}cyclopropanecarboxamide | HCID 59334617 | 88% |
Reaction Steps
To a suspension of 1-[(1R,2R)-2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine dihydrochloride (750 mg, 2.74 mmol) and triethylamine (1.52 mL, 10.9 mmol) in tetrahydrofuran (27 mL) was added cyclopropanecarbonyl chloride (372 μL, 4.10 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Ethanol was added to the reaction solution. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) to give the title compound (647 mg, yield 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08110585B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-b2771dda276547ca9cc2e0fadb2a917f |
| Source note | uspto-grants-2012_02 |