1,2-Dichloroethane → 2-Chloro-6-{[3-(2-pyridinyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]carbonyl}benzonitrile

Participants

Reaction Steps

EDC (174 mg, 0.909 mmol) followed by HOBT (127 mg, 0.826 mmol) was added to a suspension of 3-(2-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (I101) (166 mg, 0.826 mmol) and 3-chloro-2-cyanobenzoic acid (I125) (150 mg, 0.826 mmol) in Dichloromethane (DCM) (4 mL) and N,N-dimethylformamide (DMF) (1 mL) and the reaction was stirred at room temperature for 18 h. LCMS indicated that the major peak was the desired product. The solvent was evaporated and the residue partitioned between EtOAc and sat. NaHCO3 and the organic layer was collected. This was dried (Na2SO4) and the solvent evaporated to afford an orange oil. This was purified by MDAP to afford a pale yellow oil which solidified on standing to afford 174 mg of desired product.

Provenance & Evidence