Oxalyl chloride → HCID 67287755, compound

Participants

Reaction Steps

4-(6-cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (20 mg, 0.057 mmol) was diluted with DCM (1 ml) followed by the addition of oxalyl chloride in DCM (2M) (31 μl, 0.062 mmol) and DMF (1 drop). After stirring for 15 minutes, 2-amino-5-phenyl-[1,3,4]-thiadiazole (10 mg, 0.057 mmol) and DIEA (25 μl, 0.14 mmol) were added. After stirring for 12 hours, the reaction was loaded directly onto a biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 6-cyano-7-(4-(5-phenyl-1,3,4-thiadiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (17 mg, 0.033 mmol, 59% yield).

Provenance & Evidence