Morpholine → HCID 178509938, compound

Participants

Reaction Steps

A solution of N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-4-formyl-1H-imidazole-2-carboxamide (0.11 mmol), morpholine (0.020 mL, 0.22 mmol), NaBH(OAc)3 (0.047 g, 0.22 mmol) in CH2Cl2 (1.5 mL) was stirred at RT overnight. Sat'd NaHCO3 was added and the solution was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) and silica gel chromatography to afford the title compound (0.006 g, 11%) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.55 (t, J=1.47 Hz, 1H), 7.36-7.42 (m, 2H), 7.28 (t, J=2.06 Hz, 1H), 7.22-7.25 (m, 1H), 7.20 (br. s., 1H), 4.63 (s, 2H), 3.65-3.75 (m, 4H), 3.54 (br. s., 2H), 2.44-2.60 (m, 4H). ES-LCMS: m/z 504.1, 506.0 (M+1).

Provenance & Evidence