HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,4-Dioxane hydrochloride → N-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,4-Dioxane hydrochloride | HCID 20443148 | — |
| Reactant | (R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate | HCID 117652897 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride | HCID 117652786 | — |
Reaction Steps
To a solution of the compound from Step 2 (R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate (737 mg, 1.44 mmol) in 1,4-dioxane (10 mL) was added HCl/1,4-dioxane (7.2 mL of 4 M, 28.8 mmol) dropwise at 0° C. The reaction was stirred at room temperature for 3 h. The resulting mixture was concentrated under reduced pressure. The crude product was purified by preparatory HPLC to deliver the hydrochloride salt of the title compound (325 mg, 52%) as a yellow solid
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09227956B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-00157e2141d0416ab153753ad06a4e6c |
| Source note | uspto-grants-2016_01 |