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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588388Generated: October 27, 2026

1,4-Dioxane hydrochloride → N-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride

https://huagongshe.com/reaction/588388

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,4-Dioxane hydrochlorideHCID 20443148—
Reactant(R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylateHCID 117652897—
Solvent1,4-DioxaneHCID 31275—
ProductN-(3-methylpyridin-2-yl)-N-[(3R)-piperidin-3-yl]-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochlorideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227956B2
Source datasetuspto-grants-2016_01
ORD IDord-00157e2141d0416ab153753ad06a4e6c
Source noteuspto-grants-2016_01