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

HRID 63072Notes

Reaction equation

HRID 63072 reaction equation
Cl.[CH3:2][C:3]1([CH2:13][NH2:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.F[C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>>[CH3:2][C:3]1([CH2:13][NH:14][C:21]2[CH:22]=[N:23][CH:24]=[CH:16][C:17]=2[C:18]([OH:20])=[O:19])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 71758038(1-Methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanamine hydrochloride

Product 1

HCID 867282113-{[(1-Methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}pyridine-4-carboxylic acidYield 8%

Procedure

The title compound was prepared in 8% yield from 1-(1-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)methanamine hydrochloride and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 5. 1H NMR (400 MHz, DMSO-d6): δ 13.24 (br s, 1H), 8.31 (s, 1H), 7.78 (d, 1H, J=5.0 Hz), 7.48 (d, 1H, J=5.0 Hz), 7.45 (br s, 1H), 7.42 (d, 1H, J=7.3 Hz), 7.05-7.15 (m, 3H), 3.44-3.57 (m, 2H), 2.72 (t, 2H, J=6.4 Hz), 1.59-1.92 (m, 4H), 1.32 (s, 3H). [M+H] calc'd for C18H20N2O2, 297. found 297.

Sources & evidence

ORD record
ord-5c975d8f08d14938831702685b8fad05
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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