Trifluoroacetic acid → HCID 178496095, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-1H-pyrazol-5-amine (115 mg, 0.42 mmol), 3-chloro-4-hydroxybenzaldehyde (100 mg, 0.64 mmol) and trifluoroacetic acid (3 mL) was heated at 70° C. for 18 hours. The reaction mixture was concentrated, dissolved in 10 mL of N,N-dimethylformamide and purified by preparatory HPLC (Shimadzu LC-8A HPLC, Waters Xterra C18 30 mm×100 mm column, acetonitrile-water-trifluoroacetic acid eluent). After concentration and lyophillization of the pure fractions a yellow powder was obtained. The solid was dissolved in 4 mL of 1:1 methanol: 4M hydrogen chloride in dioxane, and evaporated to dryness (repeated three times) yielded 2-chloro-4-(1-methyl-9-(methyloxy)-8-{[2-(methyloxy)ethyl]oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol hydrochloride salt (76 mg, 0.17 mmol, 40% yield) 1H NMR (400 MHz, d6-DMSO): 10.82 (b, 1H), 7.80-7.78 (d, 1H), 7.65 (s, 1H), 746-7.44 (m, 2H), 7.18-7.16 (d, 1H), 4.37-4.35 (m, 2H), 3.94 (s, 3H), 3.78-3.76 (m, 2H), 3.36 (s, 3H), 2.83 (s, 3H); MS (EI) for C21H20ClN3O4: 414 (MH+).

Provenance & Evidence