2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86642094, compound

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Reaction Steps

A solution of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl){1-[(4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl)methyl]-4-piperidinyl}carbamate (80 mg, 0.145 mmol) and DDQ (49.4 mg, 0.218 mmol) in 1,4-dioxane (5 ml) was stirred at 120° C. for 2 h. A further 0.5 eq of DDQ (17 mg) was added and the solution stirred for a further 2 h. The mixture was allowed to cool to rt and was treated with sat NaHCO3 (10 ml). The aqueous layer was extracted with 20% MeOH/DCM (3×100 ml). The organic layers were combined, dried MgSO4, filtered and concentrated to afford the crude product (64 mg, 83%).

Provenance & Evidence