Sodium Hydroxide → HCID 69480991, compound

HRID 2364523Notes

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:34])=[C:14]([C:27]([NH:29][CH2:30][CH2:31][O:32][CH3:33])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+:36]>>[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]([O-:34])=[C:14]([C:27]([NH:29][CH2:30][CH2:31][O:32][CH3:33])=[O:28])[C:15](=[O:26])[N:16]3[CH2:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.[Na+:36]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69480992HCID 69480992, compound

Product 1

HCID 69480991HCID 69480991, compoundYield 89%

Procedure

In a manner similar to that described in example 474, from 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[(1-methyl-1H-imidazol-2-yl)methyl]-N-[2-(methyloxy)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (506 mg, 1.09 mmol described in example 467) and 1 N sodium hydroxide (1.06 mL) was prepared sodium 7-[(4-fluorophenyl)methyl]-1-[(1-methyl-1H-imidazol-2-yl)methyl]-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-4-olate (473 mg, 89% yield) as a white solid. 1H NMR (DMSO-d6) δ 10.72 (s, 1 H), 8.14 (s, 1 H), 7.92 (s, 1 H), 7.27-7.23 (m, 2 H), 7.08-7.03 (m, 2 H), 6.96 (s, 1 H), 6.71 (s, 1 H), 5.34 (s, 2 H), 3.94 (s, 2 H), 3.59 (s, 3 H), 3.38-3.33 (m, 4 H), 3.23 (s, 3 H); MS m/z 466 (M+1).

Sources & evidence

ORD record: ord-e2f5efb901b74bfb921e6099f764254b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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