2-Methoxyethylamine → HCID 69480988, compound

HRID 2364270Notes

Reaction equation

HRID 2364270 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:24])=[C:14]([C:20](OC)=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.[CH3:29][O:30][CH2:31][CH2:32][NH2:33]>>[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:24])=[C:14]([C:20]([NH:33][CH2:32][CH2:31][O:30][CH3:29])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[C:4]([C:25]([F:28])([F:26])[F:27])[CH:3]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 69482880HCID 69482880, compound

Product 1

HCID 69480988HCID 69480988, compound

Procedure

This compound was prepared from methyl 7-{[4-fluoro-2-(trifluoromethyl)phenyl]methyl}-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 2-methoxyethylamine employing methods similar to those those described in Example 9 and was purified by recrystallization from DMSO and MeOH. The product was obtained as a white solid: 1H NMR (d6-DMSO) δ 11.72 (1H, s), 10.28 (1H, brt, J=5 Hz), 8.47 (1H, s), 7.67 (1H, dd, J=9.3, 2.5 Hz), 7.59-7.51 (2H, m), 7.30 (1H, s), 4.29 (2H, s), 3.52-3.46 (4H, m), 3.26 (3H, s); HRMS calcd for C20H17F4N3O4+H+: 440.1233. Found: 440.1224.

Workup

  1. customwas purified by recrystallization from DMSO and MeOH
  2. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-7a6feed94040425997a48c79f313796e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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