Ethylenediamine → 2-(6-chloro-1-ethyl-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

2-(6-Chloro-1-ethyl-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (78 mg, 152 μmol) was dissolved in dichloromethane and to this was added trifluoroacetic acid (1.73 g, 1.17 mL, 15.2 mmol). The mixture was stirred for 4 h then concentrated en vacuo. The residue was diluted in dichloromethane and re-concentrated, and finally diluted again in dichloromethane and to this was added ethylenediamine (685 mg, 770 μL, 11.4 mmol). After 15 h the mixture was concentrated in vacuo, triturated with water and the collected solid was filtered and dried. The solid was purified by chromatography (Silica, SiliCycle 25 g cartridge, 0-5% methanol in dichloromethane, 15 min gradient) to give 2-(6-chloro-1-ethyl-1H-indazol-3-yl)-N-isopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (53 mg, 138 μmol, 91.1%) as a pale yellow powder. MS (M+H)+=383; 1H NMR (CDCl3) δ: 11.74 (br. s., 1H), 9.11-9.15 (m, 1H), 8.41 (d, J=8.7 Hz, 1H), 8.20 (d, J=3.0 Hz, 1H), 8.14 (d, J=7.9 Hz, 1H), 7.44 (s, 1H), 7.15 (dd, J=8.5, 1.3 Hz, 1H), 4.28-4.48 (m, 3H), 1.53 (t, J=7.2 Hz, 3H), 1.33 (d, J=6.4 Hz, 6H)

Provenance & Evidence