Ethylenediamine → HCID 71279444, compound

Participants

Reaction Steps

To a stirred solution of N-tert-butyl-2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 273 μmol) in dichloromethane (5 mL) was added trifluoroacetic acid (3.11 g, 2.1 mL, 27.3 mmol) at 20° C. After 6 h, the mixture was concentrated in vacuo. The residue was diluted with dichloromethane and concentrated again. The residue was then suspended in dichloromethane (5 mL) and ethylenediamine (1.23 g, 1.38 mL, 20.5 mmol) added. The mixture was stirred for 15 h, then concentrated in vacuo. The residue was triturated with water and the solid obtained by filtration. Purification by chromatography (silica, 25 g pre-packed SiliCycle cartridge, 0-5% methanol in dichloromethane gradient increasing over 15 min) gave N-tert-butyl-2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (63 mg, 165 μmol, 60%) as a pale yellow powder. MS (M+Na)+=405; 1H NMR (CDCl3) δ: 11.84 (br. s., 1H), 9.05 (s, 1H), 8.38 (d, J=8.7 Hz, 1H), 8.14 (d, J=3.4 Hz, 1H), 7.96 (s, 1H), 7.39 (d, J=1.5 Hz, 1H), 7.08 (dd, J=8.5, 1.7 Hz, 1H), 4.04 (s, 3H), 1.48 (s, 9H).

Provenance & Evidence