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

HRID 2364431Notes

Reaction equation

HRID 2364431 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:33])=[C:12]([C:26]([NH:28][CH2:29][CH2:30][O:31][CH3:32])=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+:37]>C(O)C>[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C:7]2[CH:16]=[C:15]3[C:10]([C:11]([O-:33])=[C:12]([C:26]([NH:28][CH2:29][CH2:30][O:31][CH3:32])=[O:27])[C:13](=[O:25])[N:14]3[CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])=[N:9][CH:8]=2)=[CH:4][CH:3]=1.[Na+:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 546955957-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 69482458Sodium 7-[(4-fluorophenyl)methyl]-3-({[2-(methyloxy)ethyl]amino}carbonyl)-2-oxo-1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-4-olate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-(4-Fluorobenzyl)-4-hydroxy-N-(2-methoxyethyl)-2-oxo-1-[2-(2-oxopyrrolidin-1-yl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxamide (693 mg, 1.436 mmol) in ethanol (20 mL) was treated with 1.009 M NaOH (1.423 mL, 1.436 mmol). The solution was evaporated in vacuo, triturated with Et2O, filtered and dried under high vacuum to provide the product as a white solid: 1H NMR (d6-DMSO) δ 10.65 (1H, s), 8.20 (1H, s), 7.73 (1H, s), 7.35 (2H, dd, J=5, 9 Hz), 7.11 (2H, t, J=9 Hz), 4.16 (2H, t, J=9 Hz), 4.02 (2H, s), 3.24-3.39 (8H, m), 3.25 (3H, s), 2.05 (2H, t, J˜9 Hz), 1.69-1.79 (2H, m); ES− MS: 483 (M−H+).

Workup

  1. customThe solution was evaporated in vacuo
  2. customtriturated with Et2O
  3. filtrationfiltered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-e82ee67625d74336b582db983279b082
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…