Ethylenediamine → HCID 71285853, 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 [(S)-1-(3-trifluoromethoxy-phenyl)-ethyl]-amide (123 mg, 0.196 mmol) was dissolved in dichloromethane (1 ml) and trifluoroacetic acid (0.6 ml, 7.9 mmol) was added. The light yellow reaction was stirred at room temperature for 2 h then concentrated. The residue was dissolved in dichloromethane (1 ml) and ethylenediamine (0.80 ml, 11.8 mmol) was added. The yellow reaction mixture 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 the solid collected was dried under high vacuum to provide 56 mg (57%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(S)-1-(3-trifluoromethoxy-phenyl)-ethyl]-amide as a light yellow powder. MS: (M+Na)+=521; 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 12.85 (br. s., 1H), 9.11 (s, 1H), 8.53 (d, J=7.8 Hz, 1H), 8.45 (s, 1H), 8.36 (dd, J=9.2, 5.2 Hz, 1H), 7.67 (dd, J=9.7, 1.9 Hz, 1H), 7.39-7.54 (m, 3H), 7.24 (d, J=7.1 Hz, 1H), 6.98 (td, J=9.0, 2.1 Hz, 1H), 5.27-5.43 (m, 1H), 4.14 (s, 3H), 1.65 (d, J=7.1 Hz, 3H).

Provenance & Evidence