Sodium Hydroxide → HCID 69481066, compound

HRID 2364273Notes

Reaction equation

HRID 2364273 reaction equation
[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])=[O:25])[C:6]1=[O:31].[OH-].[Na+:35]>CCO>[CH3:33][N:2]([CH3:1])[C:3](=[O:32])[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:13]=2)[C:8]([O-:23])=[C:7]([C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])=[O:25])[C:6]1=[O:31].[Na+:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 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 69481066HCID 69481066, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture 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 (15.5 g, 33.96 mmol) and EtOH (600 mL) was treated with 1N NaOH (39 mL, 39 mmol) and stirred 2 h at rt. The reaction mixture was partially concentrated at reduced pressure; the solid material was filtered, washed with EtOH and dried under high vacuum to afford the product as an off-white solid: 1H NMR (d6-DMSO) δ 10.60 (1H, br), 8.14 (1H, s), 7.26 (3H, m), 7.10 (2H, t, J=8.8 Hz), 4.92 (2H, s), 3.99 (2H, s), 3.36 (4H, m), 3.24 (3H, s), 3.08 (3H, s); ES− MS: 455 (M−, 100).

Workup

  1. concentrationThe reaction mixture was partially concentrated at reduced pressure
  2. filtrationthe solid material was filtered
  3. washwashed with EtOH
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-8b15175c84034b5e91aaa976fe1bf11a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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