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-c890dc19f0074ad1adeac3f8e3de5f2b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383825B2
Linked notes
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