Ethyl chloroformate → HCID 67276125, compound

Participants

Reaction Conditions

Reaction Steps

6-Acetoxy-1-naphthoic acid (200 mg, from Example 1) was mixed with DIPEA (1.2 eq) in THF and stirred at 0° C. for 10 minutes, to the reaction was added ethyl chloroformate (1 eq) slowly and further stirred for 1.5 hours from 0° C. to RT. To the reaction was added DIPEA (1.2 eq) and 3-amino-5-methylisoxazole (1.2 eq), the reaction was stirred at RT for 12 hours and mixed with EtOAc/H2O, further extracted with EtOAc and dried. The solution was evaporated and mixed with 15% KOH (2 ml) in MeOH (10 ml) further stirred at RT for 30 minutes. The solvent was evaporated and the residue was adjusted to weak acidic with 2N HCl, the solid was filtered and washed with water twice and cold MeOH to give 6-Hydroxy-N-(5-methylisoxazol-3-yl)-1-naphthamide (90 mg).

Provenance & Evidence