Isopropyl chloroformate → HCID 59511497, compound

Participants

Reaction Steps

To a solution of 1-(4-methoxy-7-(4-(piperazin-1-yl)phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (50 mg, 0.084 mmol) in THF (1 mL) and DMF (1 mL) were added TEA (0.023 mL, 0.168 mmol) and isopropyl carbonochloridate (13.42 mg, 0.109 mmol) at room temperature. The reaction was stirred for 3 hours. The reaction mixture was concentrated under reduced pressure. The resulting crude was purified by prep HPLC to give isopropyl 4-(4-(4-methoxy-3-(2-oxo-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)acetyl)-1H-pyrrolo[2,3-c]pyridin-7-yl)phenyl)piperazine-1-carboxylate (20 mg, 35%) as white solid. LCMS: m/e 680.58 (M+H)+, ret time 2.49 min (method 4). 1H NMR (500 MHz, MeOD) δ ppm 1.30 (d, J=6.10 Hz, 6H) 3.41-3.50 (m, 6H) 3.50-3.58 (m, 2H) 3.65-3.75 (m, 6H) 3.86-3.93 (m, 2H) 4.14 (s, 3H) 4.95-4.99 (m, 1H) 7.28 (d, J=8.85 Hz, 2H) 7.63 (dd, J=7.32, 4.88 Hz, 1H) 7.77 (d, J=8.55 Hz, 2H) 7.89 (d, J=7.93 Hz, 1H) 8.01 (s, 1H) 8.12-8.20 (m, 1H) 8.67 (s, 2H).

Provenance & Evidence