Sodium Hydroxide → HCID 70664978, compound

HRID 1854529Notes

Reaction equation

HRID 1854529 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2F)[N:7]=[C:6]([C:16]([O:18]CC)=[O:17])[CH:5]=1.[OH-:21].[Na+]>O1CCOCC1>[C:9]1([N:8]2[C:4]([NH:3][C:4]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:21])=[CH:5][C:6]([C:16]([OH:18])=[O:17])=[N:7]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 53302142Ethyl 5-amino-1-(2-fluorophenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 70664978HCID 70664978, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

145.3 mg (3.63 mmol, 1.2 Eq) of a 60% suspension of NaH in mineral oil are suspended in 25 ml of dioxane, 700 mg (3.03 mmol) of ethyl 5-amino-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylate are added and the resulting mixture is stirred for 10 minutes at RT: Then phenylisocanate (360.6 mg, 3.03 mmol, 1 Eq) is added and the resulting mixture is heated to 80° C. for 5 hours. After cooling 7 ml of 1M NaOH are added and the resulting mixture is stirred overnight at RT. The solvent is evaporated in vacuo and the obtained crude product is subjected to HPLC chromatography. 257 mg (26%) of the pure product are obtained.

Workup

  1. additionphenylisocanate (360.6 mg, 3.03 mmol, 1 Eq) is added
  2. temperaturethe resulting mixture is heated to 80° C. for 5 hours
  3. additionare added
  4. stirringthe resulting mixture is stirred overnight at RT
  5. customThe solvent is evaporated in vacuo
  6. customthe obtained crude product

Sources & evidence

ORD record
ord-27625576d38e4611861358c77365e4e1
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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