1,2-Dichloroethane → 2-{[(4-Fluorophenyl)methyl]oxy}-N-4-isoxazolyl-5-(1-methyl-1H-pyrazol-4-yl)benzamide

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Reaction Steps

A mixture of 2-{[(4-fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)benzoic acid (may be prepared as described in Description 121; 100 mg, 0.31 mmol), isoxazol-4-amine (38.6 mg, 0.46 mmol), HOBT (70.4 mg, 0.46 mmol) and EDC (88 mg, 0.46 mmol) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 16 hours. Water (50 ml) was added. The mixture was extracted with ethyl acetate (50 ml×3). The combined organic layers were washed with brine (50 ml), dried over Na2SO4, and concentrated to give the crude product. The crude product was purified by a prep-HPLC (instrument: Gilson GX-281; Column: Shimadzu PRC-ODS, 15.0 um, 19 mm*250 mm; Mobile Phase: A: 0.05% NH3H2O/H2O; B: CH3CN; Gradient 0-8 min 42-54% B; 8-12 min 95%; Flow Rate (ml/min) 30.00; Detective Wavelength (nm) 214; Retention Time (min) 7.5) to yield the title compound as a white solid. 17 mg.

Provenance & Evidence