Water → HCID 71285814, compound

Participants

Reaction Steps

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [2-hydroxy-1-methyl-2-(tetrahydro-pyran-4-yl)-ethyl]-amide, diastereomer B (70 mg, 0.120 mmol) was dissolved in a 4:6 solution of TFA:DCM (5.7 mL). After stirring at room temperature overnight, the volatiles were removed under reduced pressure. The crude material was then dissolved in dichloromethane and treated with ethylenediamine (722 mg, 12 mmol). After stirring at room temperature overnight, water was added and the resulting precipitate was collected by filtration to provide 30 mg (55%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [2-hydroxy-1-methyl-2-(tetrahydro-pyran-4-yl)-ethyl]-amide (diastereomer B) as an off-white solid. MS: (M+H)+=453. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.73 (br. s., 1H) 8.99-9.30 (m, 1H) 8.70 (dd, J=9.06, 5.29 Hz, 1H) 8.22-8.48 (m, 1H) 7.65 (dd, J=9.82, 1.89 Hz, 2H) 6.94-7.22 (m, 1H) 4.97 (d, J=6.80 Hz, 1H) 4.35 (m, 1H) 4.2 (s, 1H), 3.71 (m, 2H) 1.87 (d, J=13.60 Hz, 1H) 1.43-1.77 (m, 2H) 0.97-1.43 (m, 5H).

Provenance & Evidence