Diisopropylethylamine → HCID 68421046, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 500 mg of 4-[1-(2-Chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-benzoic acid ethyl ester (1.45 mMol, 1 equiv) in 10 mL of NMP was added 400 mg of cis—3,5 dimethyl piperazine (3.50 mMol, 2.41 equiv). The stirred solution was heated to 250° C. via microwave irradiation for 15 min. The crude product was precipitated by pouring into 100 mL of water and isolated by filtration. The crude product was then redissolved in 10 mL of CH2Cl2 and 2 mL of DMF. To the stirred solution was added sequentially 1 mL of Hunig's base and 500 μL of acetic anhydridide. After 3 hr at 25° C., the reaction mixture was concentrated to a dark oil and purifed by flash chromatography (10:1 CH.2Cl2:MeOH), yielding 300 mg of 4-{1-[2-(4-Acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-1H-[1,2,4]triazol-3-ylamino}-benzoic acid ethyl ester (0.647 mMol, 44% yield) as a white solid. 1H NMR (500 MHz, CDCl3) ∂ 8.44 (1H, s), 8.22 (1H, d), 8.05 (2H, d), 7.61 (3H, m), 7.27 (1H, s), 7.02 (1H, s), 6.86 (1H, d), 4.40 (2H, q), 3.50 (2H, q), 3.40 (2H, m), 3.20 (2H, m), 2.20 (3H, s), 1.40 (6H, m), 1.20 (3H, t) ppm. LC/MS: 2.68 min/464 (M+1).

Provenance & Evidence