Methyl iodide → HCID 59511499, compound

Participants

Reaction Steps

To a solution of 1-(4-methoxy-7-(1H-pyrazol-3-yl)-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 (0.069 g, 0.138 mmol) in DMF (3 mL) was added NaH (0.055 g, 1.381 mmol). The mixture was stirred for ten minutes and MeI (0.017 mL, 0.276 mmol) was added. After being stirred for 45 minutes, the mixture was quenched with water. The mixture was concentrated under reduced pressure. The resulting residue was diluted with DMF and was passed through a plug of cotton to remove solids. The DMF solution was purified by prep HPLC to give 1-(4-methoxy-7-(1-methyl-1H-pyrazol-3-yl)-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 as a light-yellow solid (0.017 g, 0.033 mmol, 33.1% yield). 1H NMR (500 MHz, DMSO-D6) δ ppm 12.37 (s, 1H) 8.67 (dd, J=4.88, 1.22 Hz, 1H) 8.33 (s, 1H) 8.13-8.18 (m, 1H) 8.05 (s, 1H) 7.93 (d, J=2.14 Hz, 1H) 7.85 (d, J=7.93 Hz, 1H) 7.64 (dd, J=7.48, 4.73 Hz, 1H) 6.99 (s, 1H) 4.05 (s, 3H) 4.00 (s, 3H) 3.70-3.74 (m, 2H) 3.40-3.48 (m, 4H) 3.24-3.29 (m, 2H). LCMS: m/e 514.38 (M+H)+, ret time 1.820 min (method 1).

Provenance & Evidence