Sodium Hydroxide → Sodium 5-(1,1-dioxido-1,2-thiazinan-2-yl)-7-[({4-fluoro-2-[(isopropylamino)carbonyl]benzyl}amino)carbonyl]-1,6-naphthyridin-8-olate

HRID 2252814Notes

Reaction equation

HRID 2252814 reaction equation
[O:1]=[S:2]1(=[O:36])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])=[O:19])[C:15]([OH:35])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[OH-].[Na+:38]>CC(C)=O>[O:36]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[C:29]([NH:31][CH:32]([CH3:34])[CH3:33])=[O:30])=[O:19])[C:15]([O-:35])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[Na+:38]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 30134005-(1,1-dioxothiazinan-2-yl)-N-[[4-fluoro-2-(isopropylcarbamoyl)phenyl]methyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide

Product 1

HCID 69178932Sodium 5-(1,1-dioxido-1,2-thiazinan-2-yl)-7-[({4-fluoro-2-[(isopropylamino)carbonyl]benzyl}amino)carbonyl]-1,6-naphthyridin-8-olate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(1,1-Dioxido-1,2-thiazinan-2-yl)-N-{4-fluoro-2-[(isopropylamino)carbonyl]benzyl}-8-hydroxy-1,6-naphthyridine-7-carboxamide (203 mg, 0.39 mmol) was suspended in acetone (2 mL) and sodium hydroxide (0.39 mL, 0.39 mmol, 1N aqueous solution) was added. The flask was gently warmed to make the solution homogeneous and the solution was then filtered through a glass fiber filter to remove any dust. The solution was stirred at room temperature until solids crashed out of solution. The solids were collected by vacuum filtration to give the title compound as a yellow solid.

Workup

  1. temperatureThe flask was gently warmed
  2. filtrationthe solution was then filtered through a glass fiber
  3. filtrationfilter
  4. customto remove any dust
  5. filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-2bc9496928ab47eaac43eadf78235904
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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