HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoyl chloride → trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | trans-1-[2-(2-Methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine | HCID 59334541 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | trans-N-{[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methyl}benzamide | HCID 66720594 | 67.3% |
Reaction Steps
To a solution of trans-1-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanamine (50.0 mg, 0.248 mmol) and triethylamine (41.6 μL, 0.298 mmol) in tetrahydrofuran (2.5 mL) was added benzoyl chloride (31.7 μL, 0.273 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 5 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate 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) 15 and silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95) to give the title compound (51.0 mg, yield 67%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08110585B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-674effc8dd26402ab8aff64b5dfe2cf7 |
| Source note | uspto-grants-2012_02 |