4-Methoxybenzylamine → 3-[(4-Methoxybenzyl)amino]pyridine-4-carboxylic acid

HRID 63038Notes

Reaction equation

HRID 63038 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.F[C:12]1[CH:20]=[N:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:17]2[CH:18]=[N:19][CH:20]=[CH:12][C:13]=2[C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 596996083-[(4-Methoxybenzyl)amino]pyridine-4-carboxylic acidYield 26%

Procedure

The title compound was prepared in 26% yield from 4-methoxybenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.17 (s, 1H), 7.81 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.29 (d, 2H, J=8.5 Hz), 6.91 (d, 2H, J=8.5 Hz), 4.47 (s, 2H), 3.73 (s, 3H). [M+H] calc'd for C14H14N2O3, 259. found 259.

Sources & evidence

ORD record
ord-2c2b4033f0a44b189c187393d427a542
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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