Nitrogen → HCID 68749804, compound

Participants

Reaction Steps

Step 4 Ethyl 2-(3-(2-(4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine]-1′-yl)thiazol-5-yl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl)acetate A mixture of 1′-(5-bromothiazol-2-yl)-4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine] (93.2 mg, 0.20 mmol), ethyl (2-oxo-2,3-dihydro-1H-imidazol-1-yl)acetate (Example 38, Step 2) (52 mg, 0.31 mmol), copper(I) iodide (39 mg, 0.21 mmol) and K3PO4 (105 mg, 0.49 mmol) was suspended in dry dioxane (2 mL). The reaction mixture was stirred under vacuum for 3 min, then the reaction mixture was backfilled with N2, treated with neat N1,N2-dimethylethane-1,2-diamine (22.9 mg, 0.26 mmol), covered with aluminum foil and stirred in an oil bath preheated at 94° C. for 3.5 h. The reaction mixture was then diluted with DCM (3 mL), washed with saturated NH4Cl (10 mL), 5% KHSO4 (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting oily residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 5-70% EtOAc/hexanes) to afford the title compound as a foam.

Provenance & Evidence