Sodium Hydroxide → [7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetic acid

HRID 2364240Notes

Reaction equation

[OH-:1].[Na+].CN(C)[C:5](=[O:34])[CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:15]=2)[C:10]([OH:25])=[C:9]([C:26]([NH:28][CH2:29][CH2:30][O:31][CH3:32])=[O:27])[C:8]1=[O:33]>>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:14]2[CH:15]=[C:16]3[C:11]([C:10]([OH:25])=[C:9]([C:26]([NH:28][CH2:29][CH2:30][O:31][CH3:32])=[O:27])[C:8](=[O:33])[N:7]3[CH2:6][C:5]([OH:34])=[O:1])=[N:12][CH:13]=2)=[CH:23][CH:22]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 588829801-[2-(Dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 59776534[7-[(4-fluorophenyl)methyl]-4-hydroxy-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetic acid

Procedure

A 4N NaOH solution (22 mL) was added dropwise to a 100° C. suspension of 1-[2-(dimethylamino)-2-oxoethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (5 g, 11 mmol; the title compound in Example 89) in DMSO (50 mL). The mixture was stirred for 1 h at 100° C., cooled to 10° C., diluted with H2O (10 mL), acidified by dropwise addition of conc. HCl (7 mL), diluted with EtOH and filtered to give the product as a white solid: 1H NMR (d6-DMSO) δ 13.22 (1H, br s), 10.18 (1H, m), 8.55 (1H, s), 8.03 (1H, s), 7.35 (2H, m), 7.11 (2H, m), 4.98 (2H, s), 4.11 (2H, s), 3.52 (4H, m), 3.28 (3H, s).

Sources & evidence

ORD record: ord-17ec14ccdd3a44848583a66fd3b4a5d5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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