3-Fluoropyridine-4-carboxylic acid → 3-{[3-(Cyclopropylmethoxy)benzyl]amino}pyridine-4-carboxylic acid

HRID 63065Notes

Reaction equation

HRID 63065 reaction equation
Cl.[CH:2]1([CH2:5][O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH2:11])[CH2:4][CH2:3]1.F[C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>>[CH:2]1([CH2:5][O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH:11][C:21]2[CH:22]=[N:23][CH:24]=[CH:16][C:17]=2[C:18]([OH:20])=[O:19])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 3453613-Fluoropyridine-4-carboxylic acidHCID 867282083-Cyclopropylmethoxy-benzylamine hydrochloride

Product 1

HCID 771065233-{[3-(Cyclopropylmethoxy)benzyl]amino}pyridine-4-carboxylic acidYield 7%

Procedure

The title compound was prepared in 7% yield from 3-cyclopropylmethoxy-benzylamine hydrochloride and 3-fluoroisonicotinic acid according to the procedure for the preparation of Example 5. 1H NMR (400 MHz, DMSO-d6): δ 8.07 (s, 1H), 7.79 (d, 1H, J=5.0 Hz), 7.57 (d, 1H, J=5.0 Hz), 7.23 (t, 1H, J=8.0 Hz), 6.89-6.95 (m, 2H), 6.79 (d, 1H, J=7.6 Hz), 4.49 (s, 2H), 3.78 (d, 2H, J=6.9 Hz), 1.15-1.21 (m, 1H), 0.51-0.57 (m, 2H), 0.27-0.32 (m, 2H). [M+H] calc'd for C17H18N2O3, 299. found 299.

Sources & evidence

ORD record
ord-eceab8b197234149a228dc48c5d60098
Source dataset
uspto-grants-2016_09
Patent number
US09447045B2

Reaction notes

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