Iodine → HCID 89717942, compound

Participants

Reaction Conditions

Reaction Steps

Iodine (27.8 mg, 0.110 mmol) was added to a 5 mL round-bottomed flask protected from light and pre-charged with methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(3-(trifluoromethyl)diaziridin-3-yl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (70 mg, 0.104 mmol) and triethylamine (43.6 μL, 0.313 mmol) in DCM (2 mL) to give a light yellow solution. After stirring at 20° C. for 15 minutes, the solvent was evaporated and the residue purified by flash chromatography to give methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (65 mg, 0.097 mmol, 93% yield) as a light yellow foam: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33 (s, 9H) 1.53 (dt, J=13.8, 7.0 Hz, 2H) 1.70-1.82 (m, 2H) 2.15 (br. s., 3H) 2.24-2.34 (m, 2H) 2.34-2.42 (m, 2H) 2.87-2.98 (m, 2H) 3.55-3.66 (m, 2H) 3.88 (s, 3H) 4.10 (s, 2H) 6.76 (br. s., 1H) 7.14 (d, J=8.2 Hz, 1H) 7.27 (s, 1H) 7.43 (t, J=7.8 Hz, 1H) 7.49-7.58 (m, 2H) 7.83 (dd, J=8.2, 1.4 Hz, 1H) 7.99 (d, J=1.4 Hz, 1H) 8.27 (d, J=8.2 Hz, 1H) 12.06 (s, 1H); MS m/z 669.2 (M+H)+; HPLC 97.6% @ 220 nm and 97.3% @ 254 nm, RT=2.18 minutes.

Provenance & Evidence