3-Fluoropyridine-4-carboxylic acid → {[(1-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)methyl]amino}pyridine-4-carboxylic acid

HRID 63083Notes

Reaction equation

HRID 63083 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH2:12][NH2:13])[CH2:4][CH2:3]1.F[C:15]1[CH:23]=[N:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18]>>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([CH2:12][NH:13][C:21]2[CH:20]=[C:16]([C:17]([OH:19])=[O:18])[CH:15]=[CH:23][N:22]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 45791428(1-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)methanamine

Product 1

HCID 118433546{[(1-Methyl-1,2,3,4-tetrahydroquinolin-4-yl)methyl]amino}pyridine-4-carboxylic acidYield 18%

Procedure

The title compound was prepared in 18% yield from 1-(1-methyl-1,2,3,4-tetrahydroquinolin-4-yl)methanamine and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 53. 1H NMR (400 MHz, DMSO-d6): δ 13.36 (br s, 1H), 8.35 (s, 1H), 7.83 (d, 1H, J=5.0 Hz), 7.72 (br s, 1H), 7.56 (d, 1H, J=5.0 Hz), 7.01-7.08 (m, 2H), 6.52-6.62 (m, 2H), 3.45-3.51 (m, 2H), 3.04-3.32 (m, 3H), 2.85 (s, 3H), 1.89-1.95 (m, 2H). [M+H] calc'd for C17H19N3O2, 298; found 298.

Sources & evidence

ORD record
ord-708023161b6644e38454ede58cadecff
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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