Acetic Acid → HCID 178432466, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of acetic acid (67 mg, 1.12 mmol) in tetrahydrofuran (7.5 ml) was added at room temperature 1,1′-carbonyl-diimidazole (193 mg, 1.19 mmol). The mixture was allowed to stir for 15 min at room temperature and afterwards for 90 min at 70° C. N-hydroxy-2-((R)-indan-1-ylamino)-4H-benzo[d][1,3]oxazine-6-carboxamidine (Example 130) (240 mg, 0.74 mmol) was added at room temperature. The mixture was allowed to stir for 1 h at room temperature, evaporated to dryness and diluted with acetic acid (10 ml). The reaction mixture was allowed to stir for 2 h at 100° C., evaporated, poured into saturated sodium hydrogen carbonate solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (1×20 ml), dried (magnesium sulfate) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane) to yield the title compound as white solid (137 mg, 53%). MS (ISP): m/e=347.1 (M+H+); m.p. 138° C.

Provenance & Evidence