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HRID 456581Erstellt: 25. Oktober 2026

Triethylamine → 4-(6-Methoxy-[1,5]naphthyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

https://huagongshe.com/reaction/456581

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
Edukt1-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 736489—
EduktMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Edukt6-Methoxy-1,5-naphthyridin-4-amineHCID 11435236—
LösungsmittelDimethylformamideHCID 6228—
Produkt4-(6-Methoxy-[1,5]naphthyridin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl esterHCID 11247158118,9%

Reaktionsbedingungen

Temperatur50 °C

Reaktionsschritte

A solution of acid (d) (7.9 g, 30 mmol) and triethylamine (4.2 ml, 3.03 g, 30 mmol) in N,N-dimethylformamide (50 ml) was treated with [O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate] (HATU) (9.5 g, 25 mmol). After 0.25 hours, amine (c) (3.5 g, 20 mmol) was added and the mixture heated at 50° C. overnight. Evaporation afforded an oil which was partitioned between ethyl acetate and dilute brine. Drying and evaporation afforded an oil (10 g) which was chromatographed on silica eluting with a 0–5% methanol in ethyl acetate gradient, affording an oil (6.0 g, 80%).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07186730B2
Quelldatensatzuspto-grants-2007_03
ORD IDord-6a7f9a51ee624bff981dc1f03edc5955
Quellennotizuspto-grants-2007_03