3-Fluoropyridine-4-carboxylic acid → 3-{[(5-Methylthiophen-2-yl)methyl]amino}pyridine-4-carboxylic acid

HRID 63067Notes

Reaction equation

HRID 63067 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][NH2:8])=[CH:4][CH:3]=1.F[C:10]1[CH:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>>[CH3:1][C:2]1[S:6][C:5]([CH2:7][NH:8][C:15]2[CH:16]=[N:17][CH:18]=[CH:10][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 4313442(5-Methylthiophen-2-yl)methanamine

Product 1

HCID 771063173-{[(5-Methylthiophen-2-yl)methyl]amino}pyridine-4-carboxylic acidYield 7%

Procedure

The title compound was prepared in 7% yield from 5-methylthiophen-2-ylmethylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.27 (br s, 1H), 7.84 (br s, 1H), 7.57 (d, 1H, J=4.8 Hz), 6.87 (d, 1H, 3.2 Hz), 6.65 (d, 1H, J=2.3 Hz), 4.65 (s, 2H), 2.38 (s, 3H). [M+H] calc'd for C12H12N2O2S, 249. found 249.

Sources & evidence

ORD record
ord-3a95ad91790945a086963c57565888b9
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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