1,3-Propanediamine → HCID 11201615, compound

Participants

Reaction Steps

2,3,4,5,6-pentafluorophenyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (0.20 g, 0.4 mmol) in THF (5 ml) was added to 1,3-propanediamine (0.35 ml, >10 eq) in THF (5 ml) and stirred at RT for 15 h. The solution was then concentrated under reduced pressure and the residue dissolved in 5% MeOH/EtOAc. The organic phase was washed with water, brine, dried (Na2SO4) and concentrated to give crude N-(3-aminopropyl)-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide which was then recrystallised (MeOH/Hexane/EtOAc) (0.04 g, 22%); m.p. 201-206° C. 1H NMR [400 MHz, (CD3)2SO] δ 8.42 (br s, 1H), 8.25 (s, 1H), 7.74 (dd, J=10.2, 1.9 Hz, 1H), 7.57 (dt, J=8.5, 0.9 Hz, 1H), 7.29 (t, J=8.5 Hz, 1H), 5.60 (d, J=0.9 Hz, 1H), 3.38 (s, 3 H, obscured), 3.3-3.25 (m, 2 H, obscured), 2.81 (t, J=7.4 Hz, 2H), 1.75 (p, J=7.4 Hz, 2H). HPLC 94.4% (254 nm). HRMS (FAB+) calcd for C16H19FIN4O2 445.0537 (M+), found 445.0543.

Provenance & Evidence