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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2426451Generated: October 31, 2026

Hexane → Methyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate

https://huagongshe.com/reaction/2426451

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHexaneHCID 8058—
ReactantTrimethylsilyldiazomethaneHCID 167693—
ReactantMethyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylateHCID 66997664—
SolventDichloromethane methanolHCID 21226129—
ProductMethyl 6-(3-chloro-4-fluorobenzyl)-4-methoxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylateHCID 66997854—

Reaction Steps

A mixture of methyl 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-[4-(methylamino)butyl]-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylate (0.68 g, 1.45 mmol; Example 1, Step 11) and a solution of trimethylsilyldiazomethane in hexane (2.2 mL, 4.35 mmol; 2M) in dichloromethane-methanol (1.5 & 4.5 mL) was stirred at room temperature for one hour. The reaction mixture was concentrated under vacuum to provide the title compound. This was used in the following step without further purification. ES MS M+1=480

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07968564B2
Source datasetuspto-grants-2011_06
ORD IDord-0091745fbd384accad5ce20dd1c832f3
Source noteuspto-grants-2011_06