1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-N-(6-Fluoropyridin-3-yl)-2-N-methyl-6-{5-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine

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Reaction Steps

6-(2,2,2-Trifluoroethoxy)pyridine-3-carboxylic acid (prepared in an analogous manner to Intermediate 206, 0.216 g, 0.051 mmol) was added to a solution of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.049 g, 0.252 mmol) in pyridine (1 mL) and the mixture was stirred at room temperature for 16 h. Further N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0255 g, 0.1 mmol) was added and the mixture was stirred at 50 C for 4 h. 4-Amino-6-[(6-fluoropyridin-3-yl)(methyl)amino]-N′-hydroxy-1,3,5-triazine-2-carboximidamide (Intermediate 156, 0.05 g, 0.18 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0163 g, 0.09 mmol) were added and the mixture was stirred at 50 C for 16 h and then at 60 C for 5 h. The mixture was dissolved in EtOAc and washed with water, and then saturated aq. ammonium chloride, saturated aq. sodium bicarbonate and then brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by preparative HPLC, Method B, to afford the title compound (0.002 g, 3%).

Provenance & Evidence