Potassium Carbonate → HCID 86700320, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 3-(1-methyl-1H-indazol-5-yl)-5,6-dihydropyrazin-2(1H)-one (160 mg, 0.70 mmol), (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (500 mg, 1.05 mmol), tris(2-(2-methoxyethoxy)ethyl)amine (60 μL, 0.2 mmol), potassium carbonate (320 mg, 2.3 mmol), and copper(I) chloride (69 mg, 0.70 mmol) in xylene (16 mL) was degassed with nitrogen, and was heated at 140° C. for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate. The mixture was filtered through a pad of celite and washed with ethyl acetate. The organic solution was washed with water and brine, and was dried over sodium sulfate. Concentration and purification with flash column chromatography (hexanes/EtOAc) gave (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxo-5,6-dihydropyrazin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate. LCMS-ESI+: calc'd for C34H34ClN5O4S: 644.2 (M+H+); Found: 644.3 (M+H+); and (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyrazin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate (40 mg). LCMS-ESI+: calc'd for C34H33ClN5O4S: 642.2 (M+H+); Found: 642.3 (M+H+).

Provenance & Evidence