Cesium carbonate → HCID 86685603, compound

Participants

Reaction Steps

Commercially available (R)-(+)-N-Boc-3-aminopyrrolidine (1.0 g, 5.3 mmol) and 3,5-dichloropyrazine-2-carbonitrile (928 mg, 5.1 mmol) were dissolved in ˜25 mL ACN. To this was added 1.4 mL DIEA. The reaction mixture was stirred at room temperature for 30 minutes. Water was added, solid precipitated and was filtered and dried to give crude B58.1 (1.56 g, 93% yield). To 120 mg B58.1 was added 100 mg 3-aminoquinoline (3-AQ), 375 mg Cs2CO3, 60 mg rac-BINAP, and 16 mg Pd(OAc)2. These solids were mixed with 10 mL dioxane and the subsequent suspension was degassed with argon for 5 minutes. The reaction mixture was heated at 100° C. for 3 hours and then cooled down to approximately 60° C. The mixture was filtered and the filtrate was concentrated to give crude B58.2. This crude product was dissolved in 3 mL TFA and 1 mL H2SO4. The mixture was heated at 70° C. for 30 minutes. Volatiles were removed and 5 mL H2O and 1 mL ACN was added to the resulting residue. Precipitate was filtered and the filtrate was subjected to rpHPLC to give the title compound. MS found for C18H19N7O as (M+H)+ 350.2.

Provenance & Evidence