Ethylenediamine → 2-[6-chloro-1-(2-dimethylamino-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide

Participants

Reaction Steps

2-[6-Chloro-1-(2-dimethylamino-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)amide (50 mg, 0.085 mmol) was combined with dichloromethane (1 mL) and trifluoroacetic acid (0.19 ml, 2.56 mmol) was added. After stirring for 2 h, the reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (1 mL). Ethylenediamine (0.17 ml, 2.56 mmol) was added. After stirring for 20 min, the reaction was concentrated in vacuo. The residue was triturated with water (2 mL). The precipitate was filtered, washed with water and dried to obtain 30 mg (73%) of 2-[6-chloro-1-(2-dimethylamino-ethyl)-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide as a yellow solid. MS: (M+H)+=456; 1H NMR (DMSO-d6) δ: 9.11 (s, 1H), 8.51 (d, J=8.5 Hz, 1H), 8.44 (s, 1H), 8.45 (s., 1H), 8.20 (d, J=8.0 Hz, 1H), 8.06 (s, 1H), 7.26 (d, J=8.3 Hz, 1H), 4.62 (br. s., 2H), 4.38 (br. s., 1H), 3.50 (dd, J=16.1, 4.0 Hz, 2H), 3.28 (s, 3H), 2.81 (br. s., 2H), 2.21 (s, 6H), 1.31 (d, J=6.5 Hz, 3H).

Provenance & Evidence