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

HRID 77419

Reaction equation

HRID 77419 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8](CC2C=C3C(=CC=2)C[C@@H](CN)CC3)[CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.COC1C=CC(CN(CC2C=C3C(=CC=2)C[C@@H](N)CC3)CC2CCOCC2)=CC=1.OC1C=CC(C(O)=O)=NC=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 2687405-Hydroxypyridine-2-carboxylic acidHCID 66663221((S)-6-{[(4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine2×HCID 66664086(S)-6-{[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)amino]methyl}-1,2,3,4-tetrahydronaphthalen-2-ylamine

Product 1

HCID 55211610N-(4-Methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)methanamine

Procedure

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.

Workup

  1. customIn Table 2, compounds which were prepared
  2. customwas reacted
  3. customfinally, the 4-methoxybenzyl group was removed

Sources & evidence

ORD record
ord-191f7116e62e45bf9699b09e7df12eaa
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Linked notes

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