反应详情

A solution of (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 80 mg, 0.31 mmol), 3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxylic acid (CAS number 1252907-86-0; 70 mg, 0.37 mmol), EDC (177 mg, 0.92 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (126 mg, 0.922 mmol) and DIPEA (161 μl, 0.92 mmol) in dry DCM (1 ml) was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate (20 ml) and water (10 ml). The organics were washed with water (2×10 ml), brine (10 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica, 0 to 100% ethyl acetate/petrol) followed by a trituration in pentane/diethyl ether to afford the title compound. 1H NMR (400 MHz, DCM-d2) δ ppm 1.43 (s, 3H), 1.66-1.99 (m, 4H), 2.14-2.30 (m, 1H), 2.49-2.68 (m, 1H), 4.40-4.55 (m, 1H), 7.38-7.48 (m, 1H), 7.56 (br. s., 1H), 7.62-7.67 (m, 1H), 7.69 (br. s., 1H), 7.84 (s, 2H), 8.08-8.14 (m, 1H), 8.23 (br. s., 1H), 8.65-8.70 (m, 1H)

1. customThe mixture was partitioned between ethyl acetate (20 ml) and water (10 ml)
2. washThe organics were washed with water (2×10 ml), brine (10 ml)
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was purified by column chromatography (silica, 0 to 100% ethyl acetate/petrol)