3-(Trifluoromethyl)phenyl isocyanate → N-[4-Methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)phenyl]-N'-[3-(trifluoromethyl)-phenyl]urea

Participants

Reaction Steps

To 1-isocyanato-3-(trifluoromethyl)benzene (8.7 μl, 0.062 mmol) was added a solution of 4-methyl-3-(9H-pyrimido[4,5-b]indol-7-yl)aniline (17.0 mg, 0.062 mmol) and DIPEA (16 μL, 0.089 mmol) in THF (0.4 mL). The reaction was stirred at ambient temperature until LCMS indicated complete reaction, typically 3-4 hours. The reaction mixture was diluted to a total of 2 mL with THF and MeOH and purified by preparative LCMS to recover the product as a TFA salt (16.7 mg, 46.9%). 1H NMR (400 MHz, CDCl3): δ 13.0 (bs, 1H), 9.65 (s, 1H), 9.15 (s, 2H), 8.93 (s, 1H), 8.37 (d, 1H), 8.01 (s, 1H), 7.4-7.6 (m, 5H), 7.2-7.4 (m, 3H), 2.21 (s, 3H). MS (EI) m/z=462 (M+H).

Provenance & Evidence