4-(Trifluoromethyl)benzylamine → 3-{[4-(Trifluoromethyl)benzyl]amino}pyridine-4-carboxylic acid

HRID 63039Notes

Reaction equation

HRID 63039 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.F[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:19]2[CH:20]=[N:21][CH:22]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 768044-(Trifluoromethyl)benzylamineHCID 3453613-Fluoropyridine-4-carboxylic acid

Product 1

HCID 817533373-{[4-(Trifluoromethyl)benzyl]amino}pyridine-4-carboxylic acidYield 28%

Procedure

The title compound was prepared in 28% yield from 4-(trifluoromethyl)-benzylamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 3. 1H NMR (400 MHz, DMSO-d6): δ 8.10 (br s, 1H), 8.04 (s, 1H), 7.83 (d, 1H, J=5.0 Hz), 7.81 (d, 2H, J=8.0 Hz), 7.58 (d, 1H, J=5.0 Hz), 7.54 (d, 2H, J=8.0 Hz), 4.69 (s, 2H). [M+H] calc'd for C14H11F3N2O2, 297. found 297.

Sources & evidence

ORD record
ord-8800806044b842208011b910053aeecd
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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