Triethylamine → 1-(4-Methoxyphenyl)-1H-pyrazole

HRID 2186239Notes

Reaction equation

HRID 2186239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11](C(OCC)=O)=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.Cl.NO>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 143726701-[(4-methoxy)phenyl]-3-(ethoxycarbonyl)-1H-pyrazole

Product 1

HCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleYield 69.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-[(4-methoxy)phenyl]-1H-pyrazole-5-[(4-(N-pyrrolidinocarbonyl)phenyl)carboxyamide-3-carboxylic acid (100 mg, 0.23 mmol) in 5 mL of acetonitrile was added triethylamine (0.064 mL, 0.46 mmol) and iso-butyl chloroformate (0.030 mL, 0.23 mmol). After stirring at ambient temperature for 30 min, there was added hydroxylamine hydrochloride (16 mg, 0.23 mmol). The reaction was stirred for 1 h and then the volatiles were removed. The residue was purified by prep HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and lyophilized to afford 28 mg (27%) of the title compound as a white powder. LRMS (ES−): 562.1 (M−H+TFA)−.

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customthe volatiles were removed
  3. customThe residue was purified by prep HPLC (
  4. washC18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and

Sources & evidence

ORD record
ord-707397dab7a94194bbe6c428dfab08fb
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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