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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1056651Generated: November 5, 2026

Triethylamine → 3-(9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile

https://huagongshe.com/reaction/1056651

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantCyanoacetic acidHCID 9740—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
ReactantHOAtHCID 181649—
ReactantN2-(2,3-dimethyl-2H-indazol-6-yl)-5-methyl-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamineHCID 118406574—
Solventdichloromethane N,N-dimethylformamideHCID 22350042—
Product3-(9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrileHCID 11839017420.5%

Reaction Steps

To a solution of N2-(2,3-dimethyl-2H-indazol-6-yl)-5-methyl-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (203.2 mg, 0.4843 mmol), HOAT (105.8 mg, 0.7773 mmol) and EDCI (144.5 mg, 0.7538 mmol) in DCM/DMF (4 mL/1 mL) were added N,N-diethylethanamine (209.1 mg, 2.066 mmol) and 2-cyanoacetic acid (48.1 mg, 0.565 mmol). The reaction was stirred at rt for 2.5 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a light pink solid (48.4 mg, 20.4%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09399637B2
Source datasetuspto-grants-2016_07
ORD IDord-f9dadb5409e84c61a41af159c647a119
Source noteuspto-grants-2016_07