Trifluoroacetic acid → HCID 135912156, compound

Participants

Reaction Steps

To a mixture of 3-(3,5-dichloro-4-(4-methoxybenzyloxy)phenyl)-1H-pyrazole-5-carboxylic acid (0.05 g, 1.15 mmol) in a mixture of CH2Cl2 (2 mL) and methanol (0.5 mL) under N2 was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (0.07 g, 0.35 mmol), 2-hydroxypyridine 1-oxide (0.04 g, 0.35 mmol) and N-methylmorpholine (0.03 mL, 1.15 mmol). The mixture was stirred at room temperature for 30 minutes before addition of 3,3-diphenylpropylamine (48.1 μL, 0.23 mmol). The reaction mixture was then stirred at room temperature for 20 h. The reaction mixture was extracted with water (5 mL) and the organic layer dried via hydrophobic frit washing with CH2Cl2 (2×5 mL). The crude reaction mixture was treated with trifluoroacetic acid (0.5 mL) and stirred at room temperature for 6 h. The solution was concentrated and the residue purified by preparative HPLC to give 0.02 g (32%) of the Compound 3 as a pale brown solid. 1H NMR δ (ppm) (DMSO-d6): 2.30 (2H, q, J=6.80 Hz), 3.16 (2H, q, J=6.80 Hz), 4.03 (1H, t, J=7.59 Hz), 7.15-7.21 (2H, m), 7.26-7.37 (9H, m), 7.78 (2H, s), 8.40 (1H, s), 10.50 (1H, s), 13.50 (1H, s). LCMS (10 cm_ESI_formic_MeOH) tR 4.52 min; m/z 466/468/470 [M+H]+.

Provenance & Evidence