Cyclopropanemethanamine → HCID 71280490, compound

Participants

Reaction Steps

To a stirred mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (0.07 g, 0.15 mmol) and HATU (0.07 g, 0.18 mmol) in DMF (4.0 mL) was added N,N-diisopropyl-ethylamine (0.024 g, 0.032 mL, 0.18 mmol). After 30 min, cyclopropylmethanamine (0.016 g, 0.23 mmol) was added. After 18 h the reaction mixture was diluted with ethyl acetate and water. The aqueous phase was extracted with EtOAc then the combined organic phase was washed with water and brine, dried (MgSO4). filtered and concentrated. The residue was purified by chromatography (silica, 24 g Analogix column, 30-100% EtOAc in hexanes, gradient over 40 min) to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(cyclopropylmethyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.049 g, 0.096 mmol, 63%) as a white solid. 1H NMR (CDCl3) δ: 9.25 (s, 1H), 8.47 (d, J=8.8 Hz, 1H), 8.30-8.39 (m, 2H), 7.49 (s, 1H), 7.21 (d, J=8.8 Hz, 1H), 5.73 (s, 2H), 4.17 (s, 3H), 3.59 (t, J=8.2 Hz, 2H), 3.42-3.54 (m, 2H), 1.22 (dd, J=13.1, 6.5 Hz, 1H), 0.95 (t, J=8.0 Hz, 2H), 0.66 (d, J=7.5 Hz, 2H), 0.40 (d, J=4.3 Hz, 2H), −0.04 (s, 9H)

Provenance & Evidence