2-Methoxyethylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1H-1,5-naphthyridine-3-carboxamide

HRID 2364131Notes

Reaction equation

HRID 2364131 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:23])=[C:12]([C:18](OCC)=[O:19])[C:13](=[O:17])[NH:14]3)=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:26][O:27][CH2:28][CH2:29][NH2:30]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:23])=[C:12]([C:18]([NH:30][CH2:29][CH2:28][O:27][CH3:26])=[O:19])[C:13](=[O:17])[NH:14]3)=[N:9][CH:8]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 547199867-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1H-1,5-naphthyridine-3-carboxamide

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 7-(4-fluorobenzyl)-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (35 mg, 0.102 mmol) and 2-methoxyethylamine (384 mg, 5.11 mmol) was heated at 120° C. in a sealed tube for 18 h. The material was triturated with hot EtOH and filtered to give the product as a white solid: 1H NMR (d6-DMSO) δ 8.37 (1H, br), 7.39 (1H, br), 7.31 (2H, br t, J˜8 Hz), 7.15 (2H, br t, J˜9 Hz), 4.07 (2H, br), 3.47 (4H, br), 3.33 (3H, s); HRMS calcd for C19H18FN3O4+H+: 372.1360. Found: 372.1372.

Workup

  1. customThe material was triturated with hot EtOH
  2. filtrationfiltered

Sources & evidence

ORD record
ord-52fb3b59586340a2965c35124961733b
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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