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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 524928Generated: October 29, 2026

Ammonium formate → 2-amino-N-(4-(4-(azetidin-1-yl)piperidin-1-yl)pyridin-3-yl)-6-chloropyrazolo[1,5-a]pyrimidine-3-carboxamide

https://huagongshe.com/reaction/524928

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium formateHCID 2723923—
Reactant2-amino-6-chloro-N-(4-(4-oxopiperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 86720981—
Reactant1H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylateHCID 90199892—
SolventTolueneHCID 1140—
Product2-amino-N-(4-(4-(azetidin-1-yl)piperidin-1-yl)pyridin-3-yl)-6-chloropyrazolo[1,5-a]pyrimidine-3-carboxamideHCID 86720983—

Reaction Steps

A solution of 2-amino-6-chloro-N-[4-(4-oxo-1-piperidyl)-3-pyridyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (50 mg, 0.1296 mmol), azetidine (Hydrochloric Acid (1)) (12.12 mg, 0.1296 mmol) and ammonium formate (8.172 mg, 0.1296 mmol) in toluene was heated at reflux for 1 h with a Dean-Stark apparatus. The reaction was cooled to room temperature and evaporated. The resulting yellow solid was dissolved in DMSO and purified by fractionlynx to yield 2-amino-N-(4-(4-(azetidin-1-yl)piperidin-1-yl)pyridin-3-yl)-6-chloropyrazolo[1,5-a]pyrimidine-3-carboxamide as a white solid. (27 mg, 31%). MS (ES+) 427.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09340546B2
Source datasetuspto-grants-2016_05
ORD IDord-bee7f12c3a104691bc8716e3dfea91a3
Source noteuspto-grants-2016_05