Ethylenediamine → HCID 71285651, compound

Participants

Reaction Steps

In a 10 ml round-bottomed flask, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-hydroxy-1-methyl-ethyl)-cyclobutyl]-amide (140 mg, 0.24 mmol) was dissolved in dichloromethane (1.2 ml) and trifluoroacetic acid (0.75 ml, 9.7 mmol) was added. The orange reaction mixture was stirred at room temperature for 3 h then concentrated. The residue was dissolved in dichloromethane (1.2 ml) and ethylenediamine (1.0 ml, 14.8 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 then dried under high vacuum to provide 67 mg (63%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-hydroxy-1-methyl-ethyl)-cyclobutyl]-amide as a light yellow powder. MS: (M+Na)+=445; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 9.11 (s, 1H), 8.53 (dd, J=8.9, 5.5 Hz, 1H), 8.41 (s, 1H), 8.31 (s, 1H), 7.68 (dd, J=9.8, 2.3 Hz, 1H), 7.08-7.23 (m, 1H), 4.99 (br. s., 1H), 4.15 (s, 3H), 2.38-2.62 (m, 4H), 1.84-2.02 (m, 1H), 1.66-1.83 (m, 1H), 1.23 (s, 6H).

Provenance & Evidence