Sodium Hydroxide → sodium 1-ethyl-7-[(4-fluorophenyl)methyl]-3-({[(1S)-2-hydroxy-1-methylethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate

HRID 2364210Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:21])=[C:5]([C:22]([NH:24][C@@H:25]([CH3:28])[CH2:26][OH:27])=[O:23])[C:4]1=[O:29])[CH3:2].[OH-].[Na+:31]>>[CH2:1]([N:3]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[CH:11]=2)[C:6]([O-:21])=[C:5]([C:22]([NH:24][C@@H:25]([CH3:28])[CH2:26][OH:27])=[O:23])[C:4]1=[O:29])[CH3:2].[Na+:31]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 694801951-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 69480878sodium 1-ethyl-7-[(4-fluorophenyl)methyl]-3-({[(1S)-2-hydroxy-1-methylethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olateYield 78%

Procedure

In manner similar to that described in example 474, from 1-ethyl-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[(1S)-2-hydroxy-1-methylethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (757 mg, 1.90 mmol described in example 576) and 1 N sodium hydroxide (1.84 mL) was prepared sodium 1-ethyl-7-[(4-fluorophenyl)methyl]-3-({[(1S)-2-hydroxy-1-methylethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (626 mg, 78% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.43 (d, J=7.2 Hz, 1 H), 8.14 (s, 1 H), 7.59 (s, 1 H), 7.33-7.29 (m, 2 H), 7.12-7.07 (m, 2 H), 4.83 (m, 1 H), 4.10-4.03 (m, 4 H), 3.91 (m, 1 H), 3.40 (m, 1 H), 3.25-3.22 (m, 2 H), 1.07-1.03 (m, 5 H); MS m/z 422 (M+23).

Sources & evidence

ORD record: ord-790d2d030e06491a94e08f2783fe01d2
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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