2-Fluoro-4-(trifluoromethyl)benzoyl chloride → HCID 68520361, compound

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Reaction Steps

1-(4-Amino-3-methoxyphenyl)-3-iodo-1H-pyrazolo[4,3-d]pyrimidin-7-amine (80 mg, 0.209 mmol) in dichloromethane (5 mL) and pyridine (0.5 mL) was cooled to 5° C. in an ice bath then 2-fluoro-4-(trifluoromethyl)benzoyl chloride (52 mg, 0.230 mmol) was added dropwise. The solution was warmed to ambient temperature for 30 minutes then the solvents were removed by evaporation. The residue was dissolved in methanol (10 mL), 10% palladium on carbon (50 mg) was added and the mixture was hydrogenated at atmospheric pressure and 60° C. for 1 hour. The catalyst was removed by filtration through a pad of diatomaceous earth then the filtrate was concentrated and the material purified by preparative reverse phase chromatography. Lyophilization yielded the title compound (25 mg) as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 9.98 (s, 1H), 8.32 (m, 3H), 7.99 (t, 1H), 7.89 (d, 1H), 7.75 (d, 1H), 7.32 (d, 1H), 7.18 (m, 1H), 6.7 (bs, 2H), 3.93 (s, 3H), 1.60 (s, 3H); RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 18.75 min; MS: MH+ 447.1, M−H+ 445.1

Provenance & Evidence