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

Participants

Reaction Steps

In a round-bottomed flask, 2-(5-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1,2,2-trimethyl-propyl)-amide (90 mg, 0.17 mmol) was dissolved in dichloromethane (0.8 ml) and trifluoroacetic acid (0.5 ml, 6.6 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was redissolved in dichloromethane (0.8 ml) and ethylenediamine (0.7 ml, 9.9 mmol) was added. The solution was stirred at room temperature for 1.5 h then quenched with water and diluted with ethyl acetate. The resultant suspension was filtered, rinsed with hot water and ethyl acetate then dried under high vacuum to provide 60 mg (83%) of 2-(5-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1,2,2-trimethyl-propyl)-amide as a light yellow powder. MS: (M+H)+=411; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.43 (br. s., 1H), 9.08 (s, 1H), 8.45 (s, 1H), 8.33 (s, 1H), 8.00 (d, J=10.2 Hz, 1H), 7.85 (d, J=8.9 Hz, 1H), 7.55 (dd, J=8.9, 1.5 Hz, 1H), 4.20 (s, 3H), 4.06-4.28 (m, 1H), 1.33 (d, J=6.8 Hz, 3H), 0.92 (s, 9H).

Provenance & Evidence