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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 77419Generated: October 25, 2026

5-Hydroxypyridine-2-carboxylic acid → N-(4-Methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)methanamine

https://huagongshe.com/reaction/77419

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Hydroxypyridine-2-carboxylic acidHCID 268740—
Reactant((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamineHCID 66663221—
Reactant(S)-6-{[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-ylamineHCID 66664086—
ProductN-(4-Methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)methanamineHCID 55211610—

Reaction Steps

In Table 2, compounds which were prepared by reacting the appropriate acids with ((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine or, correspondingly, (S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)-amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-ylamine according to method G and subsequent detachment of the 4-methoxybenzyl group according to method F are compiled. To prepare examples 2-06, 2-07 and 2-08, ((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)-amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine was reacted according to method G with 5-hydroxypyridine-2-carboxylic acid, the resulting amide was alkylated according to method D with the appropriate alkyl bromides on the phenolic hydroxyl group, and, finally, the 4-methoxybenzyl group was removed according to method F.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841290B2
Source datasetuspto-grants-2014_09
ORD IDord-191f7116e62e45bf9699b09e7df12eaa
Source noteuspto-grants-2014_09