Furfurylamine → 7-[(4-Fluorophenyl)methyl]-N-(2-furanylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364159Notes

Reaction equation

HRID 2364159 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20](OCC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:26]([NH2:32])[C:27]1[O:31][CH:30]=[CH:29][CH:28]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([NH:32][CH2:26][C:27]4[O:31][CH:30]=[CH:29][CH:28]=4)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 3438FurfurylamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 547197297-[(4-Fluorophenyl)methyl]-N-(2-furanylmethyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and furfurylamine employing methods similar to those described in Example 2 and was obtained as an off-white solid: 1H NMR (d6-DMSO) δ 11.85 (1H, br), 10.70 (1H, br), 8.39 (1H, br s), 7.61 (1H, s), 7.40 (1H, s), 7.31 (2H, m), 7.15 (2H, t, J=8.5 Hz), 6.42 (1H, s), 6.33 (1H, s), 4.54 (2H, s), 4.08 (2H, s); HRMS calcd for C21H16FN3O4+H+: 394.1202. Found: 394.1195.

Workup

  1. customwas obtained as an off-white solid

Sources & evidence

ORD record
ord-8181cdd51b64425a9129ddfa71a5c198
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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