Sodium Hydroxide → HCID 59375647, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of N′-acetyl-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carbohydrazide (30 mg, 0.089 mmol) in ACN (1.0 mL) was added POCl3 (1.0 ml). The resulting suspension was stirred at 100° C. in a sealed vial for 3 hr. The solution was diluted with additional acetonitrile (10 mL), and then added to cooled 6N NaOH (20 mL). The resulting mixture was extracted with EtOAc (1×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford crude 1-chloro-6-isopropyl-9-(5-methyl-1,3,4-oxadiazol-2-yl)benzo[c]-1,6-naphthyridine that was used directly without further purification. LRMS (ESI) calc'd for (C18H15ClN4O) [M+H]+, 339.1; found 339.1.

Provenance & Evidence