Triethylamine → HCID 58654401, compound

Participants

Reaction Steps

2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-1-methyl-pyrrolidine-3-carboxylic acid (27.0 mg, 0.094 mmol) was dissolved in DMF (1 mL). Next, the HBTU (54.0 mg, 0.141 mmol) was added. The reaction was stirred at room temperature for 30 minutes prior to addition of 2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethylamine (17.0 mg, 0.094 mmol) and the triethylamine (50 μL). The reaction was stirred at rt for 12 h then heated to 60° C. for 16 h. After this period, the reaction mixture was transferred to a separatory funnel with ethyl acetate (20 mL). The organic layer was washed with saturated NaHCO3 (aq) (30 mL) and H2O (30 mL), respectively. The aqueous layers were back extracted with ethyl acetate and all of the organic portions were combined, dried over Na2SO4 and concentrated under vacuum. The material was purified by Flash Chromatography (10 g, 0-10% methanol/DCM gradient) to afford 3.3 mg of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-1-methyl-pyrrolidine-3-carboxylic acid [2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethyl]-amide. Product isolated as a mixture of diasteromers; [M+H]+ 449.84.

Provenance & Evidence