Ethanolamine → 1-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364275Notes

Reaction equation

HRID 2364275 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24](OCC)=[O:25])[C:6]1=[O:29].[CH2:32]([CH2:34][NH2:35])[OH:33]>>[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:35][CH2:34][CH2:32][OH:33])=[O:25])[C:6]1=[O:29]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 58882926HCID 58882926, compound

Product 1

HCID 694810091-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Procedure

This compound was prepared from ethyl 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and ethanolamine 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 10.53 (1H, br), 8.14 (1H, s), 7.26 (3H, m), 7.10 (2H, t, J=9 Hz), 4.92 (2H, s), 4.74 (1H, br t), 3.99 (2H, s), 3.45 (2H, m), 3.27 (2H, m), 3.08 (3H,), 2.78 (3H, s); HRMS calcd for C22H23FN4O5+H+: 443.1731. Found: 443.1738.

Workup

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

Sources & evidence

ORD record
ord-8e54137951d84a24a149fb8e5c1a80ee
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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