Tetrahydrofuran → N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 607382Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]([CH3:10])=[N:3]1.C1COCC1.[C:16]([C:18]1[CH:19]=[C:20]([NH2:24])[CH:21]=[CH:22][CH:23]=1)#[CH:17]>CCN(CC)CC>[C:16]([C:18]1[CH:19]=[C:20]([NH:24][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[CH:5]=2)=[O:8])[CH:21]=[CH:22][CH:23]=1)#[CH:17]

Participants

Conditions

Temperature: 55 °C

Procedure

A dry 25 mL flask was charged with 2,5-dimethyl-2H-pyrazole-3-carbonyl chloride (0.135 g, 0.854 mmol) and THF (5 mL) was added. 3-Ethynyl-phenylamine (0.100 g, 0.854 mmol) was added to the THF solution of the acid chloride followed by NEt3, and the mixture was allowed to stir at 55° C. The reaction mixture was then allowed to cool to room temperature. The reaction was extracted twice with EtOAc (5 mL) and water (10 mL) followed by saturated aqueous NaHCO3 (˜10 mL). The combined organic layers were dried over anhydrous Na2SO4 (s) and then concentrated. The crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 60%). The product containing fractions were concentrated to give the title compound as a tan solid (147 mg. 72%).

Workup

additionwas added
temperatureto cool to room temperature
extractionThe reaction was extracted twice with EtOAc (5 mL) and water (10 mL)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4 (s)
concentrationconcentrated
customThe crude residue was purified by chromatography (silica gel, gradient elution EtOAc/Hexanes 0 to 60%)
additionThe product containing fractions
concentrationwere concentrated

Sources & evidence

ORD record: ord-a0cbc91e44c442448b4e8f3b18015306
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915443B2

Reaction notes

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