Diisopropylethylamine → 1-(5-(4-fluorophenyl)-11-methyl-1-oxo-2,4,5,11-tetrahydro-1H-2,5,11-triazadibenzo[cd,h]azulen-8-yl)-3-(3-phenoxyphenyl)urea

Participants

Reaction Steps

A stock solution of Example 23e and N,N-diisopropylethylamine (0.0875 M and 0.042 in N,N-dimethylacetamide, respectively, 497 μL, 0.042 mmol Example 23e and 0.126 mmol N,N-diisopropylethylamine) and 1-isocyanato-3-phenoxybenzene (0.40 M in N,N-dimethylacetamide, 208 μL, 0.084 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 150° C., and passed through the reactor at 180 μL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to give 0.0067 g (28%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) δ 7.90 (d, J=2.44 Hz, 1H), 7.60 (s, 1H), 7.40 (m, 2H), 7.27 (m, 3H), 7.16 (m, 3H), 7.03 (m, 2H), 6.97 (s, 1H), 6.78 (m, 2H), 6.64 (m, 1H), 6.51 (m, 2H), 4.60 (m, 2H), 4.06 (s, 3H). MS (APCI+) m/z 572.1 (M+H)+.

Provenance & Evidence