Water → HCID 10303740, compound

HRID 1357231Notes

Reaction equation

HRID 1357231 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[C:24]=3[C:25]([F:28])([F:27])[F:26])=[O:19])[CH:12]=2)[C:7]=1[Br:36].[OH-].[Na+].O>CO>[Br:36][C:7]1[C:8]2[C:13](=[CH:12][C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:21]=[N:22][N:23]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[C:24]=3[C:25]([F:26])([F:27])[F:28])=[O:19])=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[O:5][CH2:4][C:3]([OH:37])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69137609HCID 69137609, compound

Product 1

HCID 10303740HCID 10303740, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [1-bromo-6-({[1-(4-chloro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-methyl)-naphthalen-2-yloxy]-acetic acid methyl ester (0.175 g, 0.29 mmol), prepared in the previous step, 1N NaOH (323 μL, 0.323 mmol), 2 mL of H2O and 100 mL of methanol was warmed until all solids had gone into solution. When the reaction cooled a solid precipitated. After the reaction had stirred for 17 h (overnight) a solid was still present. Another 162 μL (0.162 mmol) of 1N NaOH was added. The reaction stirred for 18 h. The reaction was filtered to remove any trace particles and acidified with 1N HCl until pH 1 by litmus paper. The methanol was removed under reduced pressure. The solid formed was collected by filtration and dried under reduced pressure to give the title compound (0.14 g, 8.3%) as a white solid, mp 245° C.

Workup

  1. temperaturewas warmed until all solids
  2. temperatureWhen the reaction cooled a solid
  3. customprecipitated
  4. stirringThe reaction stirred for 18 h
  5. filtrationThe reaction was filtered
  6. customto remove any trace particles
  7. customThe methanol was removed under reduced pressure
  8. customThe solid formed
  9. filtrationwas collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-48957f9705be4cf5a81695340a6e976c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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