Hydrochloric Acid → HCID 57893420, compound

Participants

Reaction Steps

Ethyl 6-cyclohexyl-2-{[4-(1,1-dimethylethyl)phenyl]methyl}-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (0.040 g of a 60% oil suspension, 1.00 mmol) was added to a stirred suspension of ethyl 6-cyclohexyl-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (example 10(a), 0.100 g, 0.376 mmol) in dimethylformamide (2.0 mL) under nitrogen. After 15 min stirring at room temperature, the mixture was cooled in an ice bath and 4-tert-butylbenzyl bromide (0.071 mL, 0.384 mmol) injected. The mixture was stirred for 0.5 h at 0° C. and 3 h at room temperature. 0.1M aqueous hydrochloric acid (50 mL) was added and the mixture extracted with ethyl acetate. The extracts were washed with dilute aqueous sodium chloride, then dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 0-6% methanol/dichloromethane) to give the title compound (0.087 g, 56%) as a gum. LCMS (ES+) m/z 413 (MH+).

Provenance & Evidence