Sodium Hydroxide → HCID 22346331, compound

HRID 897361Notes

Reaction equation

HRID 897361 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([C:21]([O:23]C)=[O:22])[C:13]3[CH:14]=[CH:15][CH:16]=[N:17][C:18]=3[C:19]=2[OH:20])=[O:9])=[C:4]([S:27][CH3:28])[CH:3]=1.[OH-].[Na+]>O1CCOCC1.CO>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([C:21]([OH:23])=[O:22])[C:13]3[CH:14]=[CH:15][CH:16]=[N:17][C:18]=3[C:19]=2[OH:20])=[O:9])=[C:4]([S:27][CH3:28])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22346305HCID 22346305, compound

Product 1

HCID 22346331HCID 22346331, compound

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 7-({[4-fluoro-2-(methylthio)benzyl]amino}carbonyl)-8-hydroxy-1,6-naphthyridine-5-carboxylate (0.180 g, 0.448 mmol) in 4 mL of dioxane: methanol (3:1) was added 1.34 mL of a stock solution of 1 N NaOH (1.34 mmol). The reaction was stirred for 3 hours at 80 degrees C. The reaction was determined to be complete by LCMS analysis. The solvent was removed in vacuo and the residue partitioned between 5% HCl and methylene chloride. The organics were reduced to give desired compound as a solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between 5% HCl and methylene chloride

Sources & evidence

ORD record
ord-70b9debe86024045b5a341c2301fd7e1
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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