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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 15296Generated: October 25, 2026

4-(N-Boc-amino)piperidine → Methyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate

https://huagongshe.com/reaction/15296

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(N-Boc-amino)piperidineHCID 723833—
ReactantMethyl 2-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoateHCID 57423102—
SolventDimethylformamideHCID 6228—
Solvent1,1,3,3-TetramethylguanidineHCID 66460—
ProductMethyl 3-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]propanoateHCID 57423104—

Reaction Conditions

Temperature70 °C

Reaction Steps

To a solution of methyl 2-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate (2.53 g, 10.37 mmol) in DMF (4 ml) and tetramethylguanidine (0.1 ml) was added 1,1-dimethylethyl 4-piperidinylcarbamate (2.08 g, 10.37 mmol). The reaction was stirred for 1 hour at 70° C. after which time the solvent was evaporated. The residue was chromatographed on silica eluting with a gradient of 5% methanol in dichloromethane affording the desired compound as a yellow solid (2.66 g, 58%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732461B2
Source datasetuspto-grants-2010_06
ORD IDord-3cf1206945f44fc7be4f7d9f075c1ab8
Source noteuspto-grants-2010_06