Serinol → HCID 71280553, compound

Participants

Reaction Steps

To a stirred mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (0.07 g, 0.15 mmol) and HATU (0.07 g, 0.18 mmol) in DMF (4.0 mL) was added N,N-diisopropyl-ethylamine (0.024 g, 0.032 mL, 0.18 mmol). The mixture was stirred at room temperature for 30 minutes then 2-aminopropane-1,3-diol (0.021 g, 0.23 mmol) was added. After 18 h the reaction mixture was diluted with ethyl acetate and water. The aqueous phase was extracted with EtOAc then the combined organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. The residue was collected by filtration, washed with dichloromethane and dried in vacuum oven to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(1,3-dihydroxypropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.035 g, 0.07 mmol, 43%) as a white solid. 1H NMR (CDCl3) δ: 9.24 (s, 1H), 8.75 (d, J=7.3 Hz, 1H), 8.57 (d, J=8.5 Hz, 1H), 8.35 (s, 1H), 7.44 (s, 1H), 7.24 (s, 1H), 5.68 (s, 2H), 4.42 (br. s., 1H), 4.14 (s, 3H), 4.01-4.12 (m, 4H), 3.57 (t, J=8.0 Hz, 2H), 2.51 (br. s., 2H), 0.94 (t, J=7.9 Hz, 2H), −0.04 (s, 9H)

Provenance & Evidence