Ethylenediamine → 2-[6-fluoro-1-(2-morpholin-4-yl-2-oxo-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Participants

Reaction Steps

In a round-bottomed flask, 2-[6-fluoro-1-(2-morpholin-4-yl-2-oxo-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (81 mg, 0.13 mmol) was dissolved in dichloromethane (0.7 ml) and trifluoroacetic acid (0.41 ml, 5.32 mmol) was added. The yellow reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was dissolved in dichloromethane (0.7 ml) and ethylenediamine (0.54 ml, 8.00 mmol) was added. The reaction was stirred at room temperature for 1 h then quenched with water and diluted with ethyl acetate. The resulting suspension was filtered and washed with hot water and ethyl acetate and dried under high vacuum to provide 38 mg (60%) of 2-[6-fluoro-1-(2-morpholin-4-yl-2-oxo-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as an off-white powder. MS: (M+Na)+=502; 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 12.81 (br. s., 1H), 9.04 (s, 1H), 8.49 (dd, J=8.8, 5.3 Hz, 1H), 8.40 (s, 1H), 7.95 (s, 1H), 7.62 (dd, J=10.0, 2.1 Hz, 1H), 7.16 (td, J=9.1, 2.3 Hz, 1H), 5.60 (s, 2H), 3.69-3.77 (m, 2H), 3.57-3.67 (m, 4H), 3.42-3.50 (m, 2H), 1.53 (s, 9H).

Provenance & Evidence