Ammonium Chloride → HCID 11639916, compound

Participants

Reaction Steps

4-[5-(1-Cyclopentyl-3-ethyl-1H-indazol-6-yl)-1H-pyrazol-1-yl]benzoic acid (7 mg, 0.02 mmol), PYBOP (14 mg, 0.026 mmol), 1.0 mL of N,N-dimethylformamide, 1-hydroxybenzotriazole (3.5 mg, 0.026 mmol), N,N-diisopropylethylamine (12 uL, 0.070 mmol) and ammonium chloride (1.9 mg, 0.035 mmol) were combined in a 1-neck round-bottom flask and stirred at room temperature for two hours. The mixture was treated with 10 mL of saturated aqueous NaHCO3 and 10 mL of ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and approximately 500 mg of silica gel was added. The mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography over silica gel eluting with a gradient of 10% ethyl acetate in hexanes for 5 minutes and then increasing linearly to 100% ethyl acetate at 25 minutes to yield 4-[5-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)-1H-pyrazol-1-yl]benzamide (5 mg, 62%) as a white solid. LC/MS (EI) tR 4.09 (Method C), m/z 400.2 (M++1). 1H NMR (CDCl3 300 MHz) δ 1.4 (t, 3H); 1.6 (m, 2H); 1.8 (m, 2H); 2.1 (m, 4H); 3.0 (q, 2H); 4.8 (m, 1H); 5.7 (br s, 1H); 6.0 (br s, 1H); 6.6 (s, 1H); 6.9 (d, 1H); 7.3-7.5 (m, 3H); 7.6 (d, 1H); 7.8 (m, 3H).

Provenance & Evidence