1,4-Cyclohexadiene → HCID 9867344, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[[3-(2-amino-1,2-dioxoethyl)-1-benzyl-2-ethyl-1H-benz[f]indol-4-yl]oxy]acetic acid benzyl ester (29 mg, 0.056 mmol), 10% palladium-on-carbon (30 mg), and 1,4-cyclohexadiene (1 mL) in tetrahydrofuran (1 mL) was warmed to 50° C. with stirring for 3 h. The mixture was filtered and the resulting solution concentrated in vacuo. The filtered solids were washed with methanol and the resulting solution concentrated in vacuo. Both residues were dissolved methylene chloride and diluted with hexane. The resulting precipitate was collected via vacuum filtration to provide 8.8 mg (37%) of the title compound as a solid: mp 243-253° C. (dec). 1H NMR (DMSO-d6) δ8.26 (m, 1H), 8.11 (bs, 1H), 7.89 (m, 1H), 7.75 (s, 1H), 7.53 (s, 1H), 7.34 (m, 2H), 7.30 (m, 2H), 7.22 (t, J=7.0 Hz, 1H), 7.07 (d, J=7.3 Hz, 2H), 5.60 (s, 2H), 4.47 (s, 2H), 2.97 (q, J=7.7 Hz, 2H), 1.10 (t, J=7.3 Hz, 3H); TOF MS ES+ exact mass calculated for C25H23N2O5: m/z=431.1607 (p+1). Found: 431.1605.

Provenance & Evidence