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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 15343Generated: October 25, 2026

Hydrochloric Acid → 3-Chloro-4-({(3r,4s)-3-hydroxy-4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochloride

https://huagongshe.com/reaction/15343

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantEther hydrochlorideHCID 10953452—
Reactant[1,3]Oxathiolo[5,4-c]pyridine-6-carbaldehydeHCID 59254367—
Reactantracemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneHCID 68685696—
SolventChloroformHCID 6212—
Product3-Chloro-4-({(3r,4s)-3-hydroxy-4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochlorideHCID 68688050—

Reaction Steps

The free base of the title compound was synthesised from racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one and [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 61) according to the general method of Example 24(b). The free base of the title compound was converted to the hydrochloride by dissolving in chloroform and adding 1 equivalent of 1M HCl/diethyl ether, then evaporating to dryness. MS as that of free base.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732461B2
Source datasetuspto-grants-2010_06
ORD IDord-8c3e57c2b7844e3fa5db393895f2250f
Source noteuspto-grants-2010_06