Dimethylformamide → HCID 86711489, compound

Participants

Reaction Conditions

Reaction Steps

To a 25° C. suspension of ethyl 5-methyl-4-(3-morpholinobenzyl)oxazole-2-carboxylate (40 mg, 0.121 mmol) and K2CO3(33.5 mg, 0.242 mmol) in DMF (1211 μl) was added (Z)—N′-hydroxy-4-(trifluoromethoxy)benzimidamide (40.0 mg, 0.182 mmol). The mixture was heated to 150° C. for 12 h. The brown mixture was cooled to RT and partitioned between EtOAc (0.5 mL) and H2O (0.5 mL). The aqueous layer was extracted with EtOAc (3×0.5 mL) and the combined organic layers were washed with H2O (3×0.5 mL) then brine (0.5 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude oil was purified by Biotage (25 g ultra SNAP; 10% EtOAc/Hexane-50% EtOAc) to provide a clear oil. Compounds was loaded onto an Agilent SCX column in MeOH, washed with MeOH until neutral pH, then eluted with 1 N NH3 in MeOH. Evaporation of the volatiles then yielded the desired compound as an orange oil: (8.7 mg, 20%): 1H NMR (600 MHz, CDCl3) δppm 8.24-8.21 (m, 2H), 7.33 (app dd, J=8.8 Hz, 0.7 Hz, 2H), 7.18 (t, J=7.9 Hz, 1H), 6.86 (app t, J=1.8 Hz, 1H), 6.79 (dd, J=8.2 Hz, 2.0 Hz, 1H), 6.73 (d, J=7.9 Hz, 1H), 3.91 (s, 2H), 3.19 (t, J=4.9 Hz, 4H), 2.55 (t, J=4.9 Hz, 4H), 2.37 (s, 3H), 2.33 (s, 3H); MS (ES+) C25H24F3N5O3 requires: 499, found: 500 [M+H]+.

Provenance & Evidence