5-Amino-2-chloropyridine → N-(6-Chloro-pyridin-3-yl)-2-(7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid, prepared as in reference 16, (25 mg, 0.091 mmol) in DMF (1 mL) is added DIEA (35.4 mg, 0.274 mmol), HATU (38.2 mg, 0.100 mmol) and 6-chloro-pyridin-3-ylamine (35.2 mg, 0.274 mmol). The mixture is stirred at room temperature for 2 hours and concentrated. The residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give N-(6-Chloro-pyridin-3-yl)-2-(7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetamide; 1H NMR (DMSO-d6) δ 3.43 (t, 2H, J=5.6 Hz), 3.84 (s, 2H), 5.96 (t, 1H, J=7.2 Hz), 7.12 (dt, 1H, J1=2.4 Hz, J2=8.8 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.46 (dd, 1H, J1=4.4 Hz, J2=8.8 Hz), 7.67 (dd, 1H, J1=2.4 Hz, J2=10.8 Hz), 8.01 (dd, 1H, J1=2.8 Hz, J2=8.0 Hz), 8.19 (t, 1H, J=5.2 Hz), 8.54 (d, 1H, J=3.2 Hz), 10.48 (s, 1H), 12.04 (s, 1H); m/z [M++1] 385.0.

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