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HCID 178470495, compound → HCID 178524954, compound

HRID 132048
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Reaction equation

HRID 132048 reaction equation
C([O:3][C:4]([C:6]1[C:10]([NH:11][C:12](=[O:21])[C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[CH:9][NH:8][N:7]=1)=[O:5])C>[OH-].[Na+].CO>[F:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([F:20])[C:13]=1[C:12]([NH:11][C:10]1[C:6]([C:4]([OH:5])=[O:3])=[N:7][NH:8][CH:9]=1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 178470495HCID 178470495, compound

Product 1

HCID 178524954HCID 178524954, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

A mixture of 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid ethyl ester (10.2 g) in 2 M aqueous NaOH/MeOH (1:1, 250 ml) was stirred at ambient temperature for 14 h. Volatile materials were removed in vacuo, water (300 ml) added and the mixture taken to pH 5 using 1M aqueous HCl. The resultant precipitate was collected by filtration and dried through azeotrope with toluene to afford 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid as a pink solid (5.70 g). (LC/MS: Rt 2.33, [M+H]+267.96).

Workup

  • customVolatile materials were removed in vacuo, water (300 ml)
  • additionadded
  • filtrationThe resultant precipitate was collected by filtration
  • dry with materialdried through azeotrope with toluene
  • Sources & evidence

    ORD record
    ord-2be4b140c6ff4dc68478b5080f7d6a92
    Source dataset
    uspto-grants-2008_06
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07385059B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes