Diisopropylamine → HCID 59784103, compound

Participants

Reaction Steps

Anhydrous DMF (20 ml) is added to a 100 ml round bottom flask containing compound 4 (325 mg, 1.014 mmol) under N2. After ten minutes diisopropylamine (0.88 ml, 5.07 mmol) is added to the flask. It is then stirred at room temperature for 1.5 hrs. (R)-1,2,3,4-Tetrahydro-1-napthylamine (149.3 mg, 1.014 mmol) is then added to the flask and stirred for 1 hr. HBTU (423.07 mg, 1.115 mmol) is added to the reaction followed by HOBT (152.1 mg, 1.126 mmol). The reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS shows completion of the reaction. It is then diluted with EtOAc and washed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude compound is flash column purified using hexane and ethylacetate gradient solvent system to yield 423 mg (93%) of the desired product 6. HPLC shows this compound to be greater than 99% pure.

Provenance & Evidence