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

HRID 63049Notes

Reaction equation

HRID 63049 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([CH3:10])[CH:3]=1.F[C:12]1[CH:20]=[N:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:17]2[CH:18]=[N:19][CH:20]=[CH:12][C:13]=2[C:14]([OH:16])=[O:15])=[C:4]([CH3:10])[CH:3]=1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 27576724-Chloro-2-methylbenzylamine

Product 1

HCID 867282033-[(4-Chloro-2-methylbenzyl)amino]pyridine-4-carboxylic acidYield 45%

Procedure

The title compound was prepared in 45% yield from 4-chloro-2-methylbenzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 13.50 (br s, 1H), 8.10 (s, 1H), 7.85 (d, 1H, J=5.0 Hz), 7.61 (br s, 1H), 7.59 (d, 1H, J=5.0 Hz), 7.31 (s, 1H), 7.19-7.25 (m, 2H), 4.52 (s, 2H), 2.34 (s, 3H). [M+H] calc'd for C14H13ClN2O2, 277, 279. found 277, 279.

Sources & evidence

ORD record
ord-e1a5247fbad64072b8ebb1caadebb01a
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

Loading…