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

HRID 2364437Notes

Reaction equation

HRID 2364437 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([NH:29][CH2:30][CH2:31][OH:32])=[O:28])[C:9]2=[O:33])=[CH:4][CH:3]=1.[OH-].[Na+:35]>C(O)C.C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([O-:26])=[C:10]([C:27]([NH:29][CH2:30][CH2:31][OH:32])=[O:28])[C:9]2=[O:33])=[CH:4][CH:3]=1.[Na+:35]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 547349691-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,5-naphthyridine-3-carboxamide

Product 1

HCID 69482746Sodium 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olateYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (311 mg, 0.690 mmol) described in example 200 was suspended in ethanol (10 mL) and 1 N sodium hydroxide was added (0.68 mL) and the resulting white suspension was stirred for 1 hour. The mixture was diluted with diethyl ether (50 mL) and the solid was collected by vacuum filtration to afford sodium 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-3-{[(2-hydroxyethyl)amino]carbonyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (300 mg, 92% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.53 (br s, 1 H), 8.15 (s, 1 H), 7.31 (m, 2 H), 7.19 (m, 2 H), 7.11 (m, 2 H), 7.03 (m, 2 H), 6.48 (s, 1 H), 4.71 (br s, 1 H), 3.85 (s, 2 H), 3.41 (m, 2 H), 3.26 (m, 2 H); MS m/z 452 (M+1).

Workup

  1. filtrationthe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-84ce5de9c2b64493b2703b9f25691db3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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