Acetamidine monohydrochloride → HCID 68312987, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 12-(benzyloxy)-13-bromo-4-iodo-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (6.13 g, 12.3 mmol), acetamidine hydrochloride (1.29 g, 13.6 mmol), Pd(OAc)2 (277 mg, 1.24 mmol), and Xantphos (1.43 g, 2.47 mmol) in DMF (20.0 mL) and TEA (5.0 mL) was heated at 40° C. under CO (1 atm) for 3 hrs. After cooling down, isopropylhydrazine hydrochloride (1.64 g, 14.8 mmol) and acetic acid (20.0 mL) were added. The resulting mixture was heated to 65° C. and stirred at this temperature for 1 hr. After removal of the solvent, the residue was poured into water (2000 mL). The solid was collected by filtration and washed with acetone to give the desired product (5.5 g, 90% yield) as a yellow solid. LCMS m/z [M+H]+ 494.1.

Provenance & Evidence