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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 872065Generated: October 30, 2026

Trifluoroacetic acid → 2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine

https://huagongshe.com/reaction/872065

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantSodium BicarbonateHCID 516892—
ReactantTert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylateHCID 71062617—
SolventDichloromethaneHCID 6344—
Product2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridineHCID 117689158—

Reaction Steps

To a solution of tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate (RR2) (38 mg, 0.08 mmol) in DCM (3 mL) was added concentrated TFA (0.5 mL, 6.5 mmol). After five minutes, saturated sodium bicarbonate (3 mL) was added and the mixture was extracted with EtOAc (3×15 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound, which was sufficiently pure to use in the subsequent step without further purification. HRMS m/z (M+H) 391.2133 found, 391.2129 required.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08975261B2
Source datasetuspto-grants-2015_03
ORD IDord-c2bf877f1ff74224a7597e095f3f4860
Source noteuspto-grants-2015_03