2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86642115, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL round-bottomed flask was added N-[((3S)-1-{[(2R)-4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-2-yl]methyl}-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamide (240 mg, 0.602 mmol) in 1,4-dioxane (5 ml) at rt under nitrogen to give a orange solution. DDQ (205 mg, 0.904 mmol) was added and the reaction became very dark. The reaction was heated to 80° C. on an oil bath and stirred for 10 h. The reaction was cooled to rt. 5% Aqueous K2CO3 (20 mL) was added and the reaction was extracted with DCM (3×100 mL). The combined organic layers were washed with a saturated aqueous NaCl solution and the organic phase was dried over Na2SO4, filtered and concentrated to give the crude product. The crude product was added to a silica gel column and was eluted with 0-20% MeOH/CHCl3 to give product (85 mg, 0.214 mmol, 35.6% yield) as an orange solid.

Provenance & Evidence