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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1056644Generated: October 31, 2026

Acetic Anhydride → 1-(9-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)ethanone

https://huagongshe.com/reaction/1056644

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
ReactantTriethylamineHCID 8471—
ReactantN4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(2,3-dimethylindazol-6-yl)pyrimidine-2,4-diamineHCID 118390164—
SolventDichloromethaneHCID 6344—
Product1-(9-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)ethanoneHCID 11839017368%

Reaction Steps

To a suspension of N4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(2,3-dimethylindazol-6-yl)pyrimidine-2,4-diamine (0.10 g, 0.23 mmol) in anhydrous DCM (10.0 mL) were added N,N-diethylethanamine (0.036 g, 0.35 mmol) and acetyl acetate (0.029 g, 0.29 mmol). The mixture was stirred at room temperature for 30 min then diluted with DCM (40 mL), washed with water (20 mL×2), followed by saturated NaHCO3 (20 mL) and brine (20 mL), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1 to 15/1) to give the title compound as a light green solid (75 mg, 68%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09399637B2
Source datasetuspto-grants-2016_07
ORD IDord-086609e477e34a639a3a01fba4108b4e
Source noteuspto-grants-2016_07