4-Methylmorpholine → HCID 178434775, compound

Participants

Reaction Conditions

Reaction Steps

3-(2,4-Difluorophenyl)-1H-thieno[2,3-c]pyrazole-5-carboxylic acid (964.9 mg, 1.877 mmol, with 4 equivalents of sodium chloride), L-(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine bis-hydrochloride (462.3 mg, 2.311 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (725.4 mg, 3.78 mmol), 1-hydroxy-7-azabenzotriazole (129.6 mg, 0.952 mmol), and N-methylmorpholine (0.826 mL, 7.51 mmol) were dissolved in N,N-dimethylformamide (18 mL) at 25° C. The reaction mixture was heated to 50° C. and allowed to stir for 10 min. The reaction was stopped, cooled to room temperature, quenched by addition of saturated aqueous ammonium chloride (15 mL), and extracted with ethyl acetate (3×15 mL). The combined organic phases were washed with saturated aqueous ammonium chloride (2×15 mL) and saturated aqueous sodium chloride (1×15 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 120 g column) on a CombiFlash purification system eluting with ethyl acetate-hexanes (0-100%). The title compound (556.0 mg, 1.428 mmol, 76% yield) was recovered as a light yellow/white solid. LC-MS [M-1-1]=390.2

Provenance & Evidence