Triethylamine → HCID 91224811, compound

Participants

Reaction Steps

A solution of 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)aniline (0.027 g, 0.07 mmol) in dichloromethane (2 mL) was treated with triethylamine (0.028 mL), followed by a solution of triphosgene (0.011 g, 0.04 mmol) in dichloromethane (1 mL). After the passage of 10 minutes, the appropriate nucleophile—in the case, methanol (excess)—was added to the 3-(6-(4-isocyanatophenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (“isocyanate”) mixture. After 10 minutes, the reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by reverse-phase high performance liquid chromatography using a Phenomenex Prodigy 21 mm×250 mm column, running a gradient elution of 5% acetonitrile/95% of 0.1% aqueous trifluoroacetic acid to 100% acetonitrile over 35 minutes to provide methyl{4-[1-isopropyl-4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}carbamate (15 mg, 48%). MS (ES+): 423.2 (M+H)+

Provenance & Evidence