Ammonia → HCID 89717640, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoro-1-((tosyloxy)imino)ethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.217 g, 0.263 mmol) in DCM (5.07 mL) was cooled to −78° C. and ammonia (1.7 mL, 79 mmol) was condensed into the sealed tube. The mixture was allowed to slowly warm to 20° C. and stirred for 3 hours. After cooling again to −78° C., the sealed tube was fitted with a septa with gas outlet and slowly warmed to 20° C. to evaporate ammonia. After 3 hours, the mixture was concentrated to dryness and then purified by flash chromatography to afford 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 (139 mg, 79% yield) as a white foam: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34 (s, 9H) 1.52-1.62 (m, 2H) 1.72-1.89 (m, 2H) 2.08-2.25 (m, 3H) 2.30-2.44 (m, 4H) 2.94 (q, J=6.4 Hz, 2H) 3.64 (q, J=6.5 Hz, 2H) 3.88 (s, 3H) 3.93 (d, J=8.4 Hz, 1H) 4.04 (d, J=8.4 Hz, 1H) 4.08 (s, 2H) 6.78 (br. s., 1H) 7.31-7.41 (m, 2H) 7.44-7.50 (m, 1H) 7.54 (t, J=5.5 Hz, 1H) 7.59 (s, 1H) 7.83 (dd, J=8.4, 1.4 Hz, 1H) 7.99 (d, J=1.4 Hz, 1H) 8.27 (d, J=8.4 Hz, 1H) 12.07 (s, 1H); MS m/z 671.4 (M+H)+; HPLC 98.6% @ 220 nm and 96.4% @ 254 nm, RT=1.91 minutes.

Provenance & Evidence