4-Methylbenzylamine → 3-[(4-Methylbenzyl)amino]pyridine-4-carboxylic acid

HRID 63057

Reaction equation

HRID 63057 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.F[C:11]1[CH:19]=[N:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]>>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:16]2[CH:17]=[N:18][CH:19]=[CH:11][C:12]=2[C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 660354-MethylbenzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 771059113-[(4-Methylbenzyl)amino]pyridine-4-carboxylic acidYield 51%

Procedure

The title compound was prepared in 51% yield from 4-methylbenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.41 (br s, 1H), 8.13 (s, 1H), 7.81 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.25 (d, 2H, J=7.9 Hz), 7.15 (d, 2H, J=7.8 Hz), 4.50 (s, 2H), 2.28 (s, 3H). [M+H] calc'd for C14H14N2O2, 243. found 243.

Sources & evidence

ORD record
ord-f5b5ba91d40b483ba752763662e7a85d
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Linked notes

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