Ethylenediamine → HCID 178435670, compound

Participants

Reaction Steps

To a solution of N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5-((2(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (45 mg, 91.3 μmol) in dichloromethane (913 μL) was added trifluoroacetic acid (417 mg, 281 μL, 3.65 mmol) and stirred at room temperature. After 16 h the reaction mixture was concentrated. The residue was dissolved in dichloromethane (913 μL) and ethylenediamine (329 mg, 370 μL, 5.48 mmol) was added and stirred at room temperature. After 1 h the reaction was diluted with 10% methanol/dichloromethane. Purification by chromatography (silica, MeOH/DCM gradient) gave N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (16 mg, 44.1 μmol, 48%) as a white solid. MS (M+H)+=363.2; 1H NMR (CD3OD) δ: 9.17 (s, 1H), 8.36 (d, J=7.5 Hz, 1H), 8.27 (s, 1H), 7.81 (s, 1H), 7.27 (d, J=7.5 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 3.03 (q, J=7.7 Hz, 2H), 1.62 (s, 9H); 1.42 (t, J=7.7 Hz, 3H).

Provenance & Evidence