Ethylene Glycol → HCID 91370646, compound

Participants

Reaction Steps

A solution of 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline (85 mg, 0.17 mmol) in tetrahydrofuran (6 mL) was treated with triphosgene (26 mg, 0.09 mmol), followed by triethylamine (0.11 mL). After the passage of five minutes, ethylene glycol (0.14 mL) was added. The mixture was concentrated to dryness under reduced pressure. The resultant residue was purified via reverse-phase high performance liquid chromatography using a Phenomenex Gemini 21 mm×100 mm column, running a gradient elution of 10% acetonitrile/90% of 0.1% aqueous trifluoroacetic acid to 70% acetonitrile over 20 minutes. After the concentration of fractions under reduced pressure, 2-hydroxyethyl(4-{4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-6-yl}phenyl)carbamate (55 mg, 56%) was obtained as clear blond semi-solid. MS (ES+): 576.1, 577.1 (M+H)+

Provenance & Evidence