3-Fluoropyridine-4-carboxylic acid → 3-[(4-Chloro-2-methoxybenzyl)amino]pyridine-4-carboxylic acid

HRID 1847161Notes

Reaction equation

HRID 1847161 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([O:10][CH3:11])[CH:3]=1.F[C:13]1[CH:21]=[N:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:18]2[CH:19]=[N:20][CH:21]=[CH:13][C:14]=2[C:15]([OH:17])=[O:16])=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 509891985-Chloro-2-methoxybenzenemethanamine

Product 1

HCID 771059083-[(4-Chloro-2-methoxybenzyl)amino]pyridine-4-carboxylic acidYield 35%

Procedure

The title compound was prepared in 35% yield from 4-chloro-2-methoxy-benzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.49 (br s, 1H), 8.10 (s, 1H), 8.00 (br s, 1H), 7.81 (d, 1H, J=5.0 Hz), 7.56 (d, 1H, J=5.0 Hz), 7.24 (d, 1H, J=8.1 Hz), 7.11 (d, 1H, J=1.9 Hz), 6.96 (dd, 1H, J=8.0, 1.9 Hz), 4.47 (s, 2H), 3.87 (s, 3H). [M+H] calc'd for C14H13ClN2O3, 293, 295. Found 293, 295.

Sources & evidence

ORD record
ord-3fdc41f16c8f44ecad994f0e26807ef6
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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