Ammonia → HCID 89719285, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(2,2,2-trifluoro-1-((tosyloxy)imino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.188 g, 0.260 mmol) in DCM (5.00 mL) cooled to −78° C., ammonia (1.689 mL, 78 mmol) was added and the tube was sealed and warmed to 20° C. The reaction mixture turned blue over time and after 3.5 hours it was cooled again to −78° C. and then slowly warmed to 20° C. with septa+nitrogen outlet to evaporate most of the ammonia. After 3.5 hours, the reaction mixture was filtered over Buchner to remove most of the ammonium p-toluenesulfonate), the solids were washed with DCM (3×1.5 mL) and the filtrate was concentrated to dryness to give a yellow foam which was purified by flash chromatography to afford methyl 4-((3-(piperidin-1-yl)propyl)amino)-2-(3-(3-(trifluoromethyl)diaziridin-3-yl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (115 mg, 78% yield) as a white foam: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31-1.43 (m, 2H) 1.50 (quin, J=5.3 Hz, 4H) 1.80 (dt, J=14.1, 7.0 Hz, 2H) 2.32 (m, J=6.7, 6.7 Hz, 6H) 3.58-3.67 (m, 2H) 3.88 (s, 3H) 3.93 (br. d, J=7.4 Hz, 1H) 4.05 (br. d, J=8.6 Hz, 1H) 4.07 (s, 2H) 7.32-7.43 (m, 3H) 7.47 (m, J=6.3 Hz, 1H) 7.59 (s, 1H) 7.81 (dd, J=8.4, 1.2 Hz, 1H) 7.99 (d, J=1.2 Hz, 1H) 8.35 (d, J=8.4 Hz, 1H) 12.07 (s, 1H); MS m/z 568.2 (M+H)+; HPLC >94%, RT=1.72 minutes.

Provenance & Evidence