Acetic Acid → HCID 18947607, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(4-chlorobenzyl)-1-[4-(quinolin-2-ylmethoxy)phenyl]hydrazine from Example 1A, Step D, (660 mg, 1.7 mmol) and anhydrous NaOAc (160 mg, 1.95 mmol) in toluene (3 mL) was added glacial HOAc (1.5 mL) . After 30 minutes, a solution containing methyl 5-(t-butylthio)-2,2-diethyl-4-oxopentanoate from Step B (402 mg, 1.47 mmol) in toluene (1 mL) was added and the reaction mixture stirred for 24 hours at room temperature and for 48 hours at 65° C. The reaction was then diluted with EtOAc, washed with NH4OAc buffer (25% w/v) and dried over MgSO4. Filtration and concentration gave a viscous oil which was purifed by flash chromatography on silica gel (eluant:EtOAc-hexane 15:85) to give the title compound.

Provenance & Evidence