Sodium Hydroxide → HCID 70664843, compound

HRID 1854531Notes

Reaction equation

HRID 1854531 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=[O:5])C.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].[OH-].[Na+]>O1CCOCC1.CO.O>[O:25]=[C:24]1[CH2:23][CH2:22][CH2:21][N:11]1[C:9]1[N:8]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 702254-Bromobutyryl chlorideHCID 23630921Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 70664843HCID 70664843, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

700 mg (3.0 mmol) of 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 20 ml of dioxane and added to a suspension of NaH (266 mg 60% suspension in mineral oil, 6.66 mmol) in 10 ml of dioxane. After stirring for 10 minutes at RT 4-bromobutyryl chloride (617.5 mg, 3.3 mmol) is added and the resulting mixture is stirred overnight at RT. A MeOH/H2O mixture (10 ml, 1:1) is added to destroy excess NaH and the solvent is removed in vacuo. The crude product is redissolved in 15 ml of EtOH and 8 mmol of 1M NaOH is added and the mixture is stirred overnight. The solvent is removed in vacuo and the residue subjected to HPLC chromatography: Yield: 554 mg, 68%

Workup

  1. additionis added
  2. customto destroy excess NaH
  3. customthe solvent is removed in vacuo
  4. dissolutionThe crude product is redissolved in 15 ml of EtOH
  5. stirringthe mixture is stirred overnight
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5cb6ae2ee42e47ac8aa2b65259da896d
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

Loading…