1,4-Dioxane → HCID 178499447, compound

Participants

Reaction Steps

Sodium tert-butoxide (0.844 mL, 6.89 mmol), [dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine]2-(2-aminoethyl)phenyl)palladium(II) chloride (125 mg, 0.157 mmol), trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (intermediate 11, 687 mg, 3.13 mmol), methyl 2-(2-chloropyridin-3-yl)acetate (640 mg, 3.45 mmol) and dry dioxane (5 mL) were sealed in a microwave vessel under argon. The mixture was stirred for 4 hours at room temperature. The reaction mixture was diluted with water (mL) and extracted with ethyl acetate. The organic extract was washed with water and dried over magnesium sulfate. Evaporation in vacuo gave the crude material as a tan solid. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g, hexane to ethyl acetate gradient), to provide methyl 2-(2-((trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)amino)pyridin-3-yl)acetate (210 mg, 0.570 mmol, 18.19% yield) and 1-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (24 mg, 0.071 mmol, 2.277% yield) as white solid. M+1: 337. 1H NMR (400 MHz, MeOH) δ ppm 2.44-2.53 (m, 2 H) 3.48-3.57 (m, 2 H) 3.62 (s, 2 H) 4.62-4.70 (m, 1 H) 5.30 (quin, J=8.66 Hz, 1 H) 7.03-7.13 (m, 2 H) 7.25-7.31 (m, 1 H) 7.48 (d, J=8.02 Hz, 1 H) 7.61-7.66 (m, 2 H) 8.22 (d, J=4.69 Hz, 1 H)

Provenance & Evidence